Tag: M.W:200-300

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 880870-13-3, name is 5-Bromo-2-chloro-4-methoxypyridine, molecular formula is C6H5BrClNO, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. Computed Properties of C6H5BrClNO

Step B: 6-Chloro-4-methoxypyridine-3-carbonitrile: A solution of 5-bromo-2-chloro-4- methoxypyridine (5.0 g, 22.48 mmol) in DMF (80 mL) was purged with nitrogen for 15 min. At this point, Zn(CN)2 (3.96 g, 33.7 mmol) and Pd(Ph3P)4 (2.60 g, 2.25 mmol) were added successively. The resulting suspension was stirred at 95 C for 12 h under nitrogen. The reaction mixture was cooled to ambient temperature, and filtered to remove inorganic solid. The solvent (DMF) was evaporated to provide the crude residue, which was purified on silica gel and eluted with 0-30% ethyl acetate / hexanes to afford the product.

With the rapid development of chemical substances, we look forward to future research findings about 880870-13-3.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DONG, Shuzhi; PASTERNAK, Alex; SUZUKI, Takao; GU, Xin; FU, Qinghong; JIANG, Jinlong; DING, Fa-Xiang; TANG, Haifeng; DEJESUS, Reynalda K.; WO2015/96035; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 77199-09-8, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 77199-09-8 as follows.

General procedure: A mixture 2a or 2b (1 g, 1 equiv.), anappropriate pinacol boronate ester (1.2 equiv.), [1,10-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex withdichloromethane (10 mol %), cesium carbonate (2.0 equiv.), 1,4-dioxane (8 ml) and water (4 ml) was sealed in a 20 ml microwavereaction vial (Biotage). The vial was irradiated in a microwaveapparatus at 110 C, normal absorption for 30-90 min. The reactionmixture was cooled to room temperature and work up was performedas described in method 1 to obtain the esters 4b-i.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,77199-09-8, its application will become more common.

Reference:
Article; Tung, Truong Thanh; Jakobsen, Tim Holm; Dao, Trong Tuan; Fuglsang, Anja Thoe; Givskov, Michael; Christensen, S°ren Br°gger; Nielsen, John; European Journal of Medicinal Chemistry; vol. 126; (2017); p. 1011 – 1020;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1207625-29-3, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 1207625-29-3, name is 5-Bromo-6-fluoro-1H-pyrrolo[2,3-b]pyridine, molecular formula is C7H4BrFN2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Into a 250-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of the commercially available 5-bromo-6-fluoro- 1H-pyrrolo[2,3-bjpyridine (CAS, 1190321-99-3, 15 g, 69.76 mmol, 1.00 equiv) in N,Ndimethylformamide (150 mL). This was followed by the addition of sodium hydride (4.2 g, 175.00 mmol, 1.50 equiv), in portions at 0 degree. After 0.5 h stirring, to this was added SEM-Cl (14 g, 84.34 mmol, 1.20 equiv) dropwise with stirring at 0 degree. The resulting solution was allowed to react, with stirring, for an additional 3 h at room temperature. The reaction was then quenched by the addition of 300 mL of water. The resulting solution was extracted with 3×200 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 3×200 mL of brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (0:1-1:10). This resulted in 15 g (62%) of 5-bromo-6-fluoro-1-[[2- (trimethylsilyl)ethoxyj methylj -1 H-pyrrolo [2,3 -bjpyridine as yellow oil. H-NMR (CDC13, 300 MHz) 6: 8.19 (d, J=8.7 Hz, 1H), 7.37 (d, J=3.6 Hz, 1H), 6.54 (d, J=3.6 Hz, 1H), 5.64 (s, 2H), 3.58 (t, J=8.1 Hz, 2H), 0.98-0.93 (t, J=8.1 Hz, 2H), 0.00 (s, 9H).

According to the analysis of related databases, 1207625-29-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NEWAVE PHARMACEUTICAL INC.; CHEN, Yi; LOU, Yan; (108 pag.)WO2019/40550; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 7477-10-3, name is 6-Chloro-5-nitronicotinic acid. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C6H3ClN2O4

[00190] To a stirred solution of 6-chloro-5-nitro-pyridine-3-carboxylic acid (500 mg, 2.46 mmol) in dioxane (5 mL) was added tert-butyl N-[(E)-4-aminobut- 2-enyl]carbamate hydrochloride (500 mg, 2.71 mmol) followed by DIPEA (1.09 mL, 6.27 mmol); mixture was stirred at RT overnight. The mixture was diluted with water and acidified to pH ~3 with 3 N HCI. The resulting suspension was filtered to give the desired product as a yellow solid, dried in oven (636 mg, 73%). 1H NMR (de-DMSO) d 13.20 (brs, 1H), 9.00 (t, J = 6 Hz, 1H), 8.89 (d, J = 4 Hz, 1H), 8.74 (d, J = 4 Hz, 1H), 6.99-6.91 (m, 1H), 5.72-5.53 (m, 2H), 4.27- 4.18 (m, 2H), 3.56-3.47 (m, 2H), 1.36 (s, 9H).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 7477-10-3, 6-Chloro-5-nitronicotinic acid.

Reference:
Patent; TRILLIUM THERAPEUTICS INC.; SLASSI, Abdelmalik; DOVE, Peter; ROSA, David Alexander; WANG, Zezhou; WINSTON, Jeffrey Todd; LIN, Hoi Ying; (0 pag.)WO2020/10451; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 887115-56-2, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.887115-56-2, name is 5-Bromo-1-methyl-1H-pyrazolo[3,4-b]pyridine, molecular formula is C7H6BrN3, molecular weight is 212.05, as common compound, the synthetic route is as follows.

Compound 1 (1.72 g, 8.11 mmol) was dissolved in DMF (20 mL) under nitrogen atmosphere, and bis(pinacolato)diboron (4.12 g, 16.2 mmol), potassium acetate (2.39 g, 24.3 mmol), and a dichloromethane adduct of [1,1?-bis(diphenylphosphino)ferrocene]palladium (II) dichloride (0.331 g, 0.406 mmol) were added thereto, followed by stirring at 90Cfor 12 hours.After the resultant reaction solution was allowed to cool, water was added thereto, followed by extraction withethyl acetate twice. The organic layer was washed with water twice and dried over anhydrous sodium sulfate, and thesolvent was distilled off under reduced pressure.The thus obtained residue was dissolved in 1,4-dioxane/water (2/1) (30 mL), and Compound V (synthesizedin accordance with the method described in WO2012/158413) (2.60 g, 8.10 mmol), tripotassium phosphate (3.44 g, 16.2mmol), chloro(2,4,6-triisopropyl-2?-dicyclohexylphosphino-biphenyl)[2-(2?-amino-1,1?-biphenyl]palladium (II) (0.128 g,0.162 mmol) were added thereto, followed by stirring at 90C for 4 hours.After the resultant reaction solution was allowed to cool, a brine was added thereto, followed by the extractionwith ethyl acetate twice, and then, the resultant was dried over anhydrous sodium sulfate, and the solvent was distilledoff under reduced pressure. The thus obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to giveCompound 2 (1.50 g, Yield 61%).1H-NMR (CDCl3) delta: 2.15 (s, 3H), 3.72 (s, 2H), 4.19 (s, 3H), 7.36-7.39 (m, 1H), 7.51 (t, J = 8.0Hz, 2H), 7.65 (d, J = 8.0Hz,2H), 8.03 (s, 1H), 8.35 (d, J = 1.6Hz, 1H), 8.93 (d, J = 1.6Hz, 1H).

Statistics shows that 887115-56-2 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-1-methyl-1H-pyrazolo[3,4-b]pyridine.

Reference:
Patent; Shionogi & Co., Ltd.; YUKIMASA, Akira; KANO, Kazuya; HORIGUCHI, Tohru; NAKAMURA, Kenichiroh; INOUE, Takatsugu; FUJIU, Motohiro; YAMAGUCHI, Hiroki; (156 pag.)EP3412663; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 867034-10-4, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 867034-10-4, name is Ethyl 7-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

Ethyl 7-chlo ro-1H-pyrrolo[2,3-c]pyridine-2-carboxylate (preparation described in Reference Example 1) (240 mg, 1.07 mmol), phenol (500 mg, 5.35 mmol) and cyclohexylamine (1.1 mL, 10.7 mmol) were combined in a sealed tube and heated at 100C for 6 h. The reaction tube was cooled to room temperature. The reaction mixture was diluted with ethyl acetate (10 mL), washed with 2 N sodium hydroxide (10 mL) and brine (10 mL), dried over magnesium sulfate, and evaporated to provide 538 mg of dark brown viscous oil. The viscous oil was purified by chromatography (Si02; 3: 1 hexanes/ethyl acetate) to give 7- chloro-N-cyclohexyl-1H-pyrrolo[2,3-c]pyridine-2-carboxamide as an off-white powder (218 mg, 0.785 mmol, 74%): ¹H NMR (300 MHz, CD30D) 81.20-1.55 (6H, m), 1.65-2.10 (4H, m), 3.90 (1H, m), 7.21 (lH, s), 7.61 (lH, d, J = 5.4 Hz), 7.93 (lH, d, J = 5.4 Hz) ; ESI MS m/z 278 [C14H16ClN3O + H](at).7-Chloro-N-cyclohexyl-1H-pyrrolo[2,3-c]pyridine-2- carboxamide (230 mg, 0.828 mmol), triethylamine (0.25 mL) and palladium (II) chloride (3 mg, 2 mol%) were combined in N,N- dimethylformamide (5 mL) under an atmosphere of hydrogen. The (at)’l’i£c£i(at)d£”‘”‘£tI%8(at)tlr(at)”(at)(at)(at)lk9″”(at)(at)ti(at)lated at 60C for 3 h. The reaction mixture was cooled to room temperature and the catalyst was removed by filtration through a pad of diatomaceous earth and washed with ethyl acetate. Evaporation of the solvents provided crude product (169 mg, 84%) as an off-white solid. Purification by chromatography (Si02; 0-10% methanol in methylene chloride, 1400 mL) afforded N-cyclohexyl-1H- pyrrolo [2,3-c]pyridine-2-carboxamide (101 mg, 0.414 mmol, 50%) as fine, white needles: mp 298-301C, ¹H NMR (300 MHz, CD30D) 8 1.20-1.55 (6H, m), 1.65-2.10 (4H, m), 3.90 (lH, m), 7.21 (1H, s), 7.15 (1H, s), 7.65 (lH, d, J = 5.7 Hz), ‘8.09 (lH, d, J = 5.7 Hz), 8.77 (lH, s) ; ESI MS m/z 244 [C14H17N3O + H] +; HPLC (Method A) >99% (AUC), tR = 13.2 min.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 867034-10-4, Ethyl 7-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylate.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2005/97129; (2005); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 127446-34-8, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 127446-34-8, name is N-(6-Chloro-3-formylpyridin-2-yl)pivalamide. This compound has unique chemical properties. The synthetic route is as follows.

A solution of 4-Benzyloxy-butan-l-ol (12) (8.43 mL, 48 mmol) in DMF (50 mL) was treated with NaH (1.52 g, 60 mmol) at O0C under nitrogen. The mixture was stirred at this temperature for 15 min, and then treated with N-(6-Chloro-3-formyl-pyridin-2-yl)-2,2- dimethyl-propionamide (11), (Journal of Organic Chemistry, 55(15), 4744-50; 1990, 5.76g, 24 mmol) in portions. After the addition was over, the mixture was left stirring for another 1 h. Aqueous NH4Cl was added to quench the reaction. The mixture was taken up into EtOAc and washed with water, dried and concentrated. The residue was purified by column chromatography on silica gel to give the title compound (13) (6.15g) 1H-NMR (400 MHz, CDCl3): 11.50 (s, IH), 9.75 (s, IH), 7.80 (d, IH), 7.40 – 7.20 (m, 5H), 6.45 (d, IH), 4.50 (m, 4H), 3.50 (t, 2H), 2.00 – 1.70 (m, 4H), 1.40 (s, 9H).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 127446-34-8, N-(6-Chloro-3-formylpyridin-2-yl)pivalamide.

Reference:
Patent; WARNER-LAMBERT COMPANY LLC; WO2006/103559; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1279815-46-1 ,Some common heterocyclic compound, 1279815-46-1, molecular formula is C9H7BrN2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

To a chilled (-78C) solution of l-(2-bromopyridin-4-yl)-cyclopropanecarbonitrile (1.16 g, 5.2 mmol) in toluene (30 mL) is added a 1 M solution of diisobutylaluminum hydride (DIBAH) (10.4 mL) in toluene. The mixture stirred at -78C for 1 hour and is then warmed to room temperature. After 1 hour, EtOAc (30 mL) is added, followed by 1 M aqueous solution of H2S04 (30 mL). The organic phase is separated and the aqueous layer is extracted with EtOAc (3 x 50 mL). The combined organic layers are dried over MgS04, filtered and concentrated to afford crude l-(2-bromopyridin-4-yl)- cyclopropanecarboxaldehyde which is used without purification. MS mJz 226.5, 228.5

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 1279815-46-1, 1-(2-Bromopyridin-4-yl)cyclopropanecarbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; COOK, Brian Nicholas; KUZMICH, Daniel; WO2011/56440; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 26163-03-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 26163-03-1, name is 3-Bromo-5-chloropyridin-2-amine, molecular formula is C5H4BrClN2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Example 39 2′-amino-6-(6-chloroimidazo[ 1 ,2-a]pyridin-8-yl)- 1 ‘,2,2-trimethylspiro[chroman-4,4′- imidazol]-5′(l’H)-oneStep A: 3-Bromo-5-chloro-2-pyridinamine (487 mg, 2.35 mmol) was diluted with ethanol (4 mL), followed by the addition of 2-chloroacetaldehyde (614 , 4.69 mmol). The reaction was heated at reflux for 3 hours. The reaction was cooled and loaded onto silica gel eluting with 10-50% ethyl acetate/hexanes to yield 8-bromo-6-chloroimidazo[l,2-a]pyridine (300 mg, 1.30 mmol, 55.2% yield).Step B: 2’-Amino-r,2,2-trimethyl-6-(4,4,5,5-tetramethyl

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 26163-03-1, 3-Bromo-5-chloropyridin-2-amine.

Reference:
Patent; ARRAY BIOPHARMA INC.; HUNT, Kevin, W.; RIZZI, James, P.; COOK, Adam; WO2011/72064; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 106961-33-5, N,N-Dimethyl-1-(6-methyl-2-(p-tolyl)imidazo[1,2-a]pyridin-3-yl)methanamine, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, Recommanded Product: 106961-33-5, blongs to pyridine-derivatives compound. Recommanded Product: 106961-33-5

Step (ii): Preparation of 6-methyl-2-(4-methylphenyl)imidazo[l,2-a|pyridine-3- acetonitrile (10)Dissolved the 6-methyl-2-(4-methylphenyl)imidazo[l,2-a]pyridine-3-N,N- dimethylmethylamine (8) ( (230 grams, 0.82 mmol) (obtained from step (i)) in dichloromethane (600 mL) under stirring. Cooled the above solution to 0 – 5 0C, add ethylchloroformate (98.4 grams, 0.90 mmol) slowly over a period of 30 minutes. Stirred the above reaction mass for a period of 45 minutes at the same temperature, distilled off the solvent under reduced pressure, which produced 332 grams crude carbamate salt of dimethylaminomethyl imidazopyridine (2) as yellow colored solid. Dissolved the obtained solid immediately in water (690 mL), basify the solution to pH 7.5-8.0 using 10% sodium hydroxide solution. Added sodium cyanide (48.4 grams, 0.99 mmol) to the above reaction mass and stirred at 50 – 55 0C for a period of 3 hours. Cooled the above reaction mass to room temperature, extracted the solution with chloroform (300 mL, 2×200 mL). Combined organic layers and washed with water (500 mL) and brine (400 mL). Dried with anhydrous sodium sulfate, filtered and concentrated the solution until the volume reaches to 250 mL. Add methanol (1000 mL), stirred for the period of 30 minutes. Filtered the formed off white solid from the solution and dried in the oven until constant weight reached. Dry weight of obtained 6- methyl-2-(4-methylphenyl)imidazo[l,2-a]pyridine-3-acetonitrile(10) is 165.0 grams. Yield: 76% Purity: 96%Melting Range: 176.9 – 178.00C;IR spectra (cm”1): 2921, 2895, 2249, 1500, 1386, 1343, 824, 799;1H NMR (400 MHz, CDCl3): delta 2.42(s, 6H), 4.13 (s, 2H), 7.16 (dd, J= 9.1 Hz, J= 1.5 Hz, IH), 7.31 (d, J= 7.9 Hz, 2H), 7.58 (d, J= 8.0 Hz, 2H), 7.60 (d, J= 9.6 Hz, IH), 7.80(s, IH);Mass (m/z): 262.5 (M+H)+; Example 2:Preparation of 6-methyl-2-(4-methylphenyl)imidazo[l,2-a]pyridine-3- acetic acid (12)Dissolved the 6-methyl-2-(4-methylphenyl)imidazo[l,2-a]pyridine (9) (100 grams, 0.45 mmol) in acetic acid (500 mL) under stirring. Cooled the reaction mass to 5 – 10 0C, added 40% aqueous solution of dimethylamine (76 grams) slowly, followed by addition of paraformaldehyde (17.7 grams). Stirred the reaction mass at 50 – 55 0C for the period of 3 hours and removed acetic acid under reduced pressure. Added water (1000 mL), basify the solution (pH 8.0) by adding 30% sodium hydroxide solution. Extracted the solution with dichloromethane (3×300 mL), washed the organic layer with water (500 mL) and brine solution (500 mL). Dry with anhydrous sodium sulfate, filtered and distilled the solvent until the volume reaches to around 300 mL. This solution contains 6-methyl-2-(4-methylphenyl)imidazo[l ,2-a]pyridine-3-N,N- dimethylmethylamine (10), 89% purity by HPLC, and used further as it is. Cooled the above organic solution to 0 – 5 0C, added ethylchloroformate (58.3 grams, 0.54 mmol) slowly over a period of 30 minutes. Stirred the reaction mass for one hour at the same temperature, distilled off the solvent under reduced pressure to obtain carbamate salt as bright yellow colored solid (2). This solid was dissolved in water (300 mL), basified the solution to pH 7.5 – 8.0 using 10% sodium hydroxide solution. Added sodium cyanide (26.5 grams, 0.54 mmol) and stirred the reaction mass at 50 – 55 0C for a period of 3 hours. Cooled the reaction mass to room temperature and filtered the yellow solid and washed with water (500 mL). This crude solid contains 6- methyl-2-(4-methylphenyl)imidazo[l,2-a]pyridine-3-acetonitrile (10), 82% purity by HPLC, and used for hydrolysis without any further purification. The above crude solid was dissolved in 50% sulfuric acid (624 mL), refluxed the reaction mass at 110 0C for 4 hours. Cooled the reaction mass to room temperature and added to a flask contain of ice cold water (2.5 L). Basified the white ppt solution by adding sodium hydroxide flakes portion wise until pH 9.0. Extracted the solution with dichloromethane (2 x 300 mL) and discarded. Added carbon (5.0 grams), stirred for 30 minutes and filtered through a pad of celite. Acidified the solution pH 5.5 by adding glacial acetic acid and obtained white solid filtered. Filtered cake was washed with water (500 mL) and dried in the airflow oven at 60 – 65 0C until constant weight reached. 78.0 grams of 6-methyl-2-(4-methylphenyl)imidazo[l,2-a]pyridine-3- aceticacid (12) obtained as off-white solid. Yield: 62.0% Purity: 99.5 %Melting Range: 234.0 – 235.20C; IR spectra (cm 1): 3427, 2919, 1701, 1508, 1183, 827, 805; 1H NMR (400 MHz, DMSO-c4): delta 2.31 (s, 3H), 2.34 (s, 3H), 4.08 (s, 2H), 7.17 (dd, J=9.1 Hz, J= 1.5 Hz, IH), 7.28 (d, J= 8.0 Hz, 2H), 7.51 (d, J= 9.1 Hz, IH), 7.61 (d, J= 8.0Hz, 2H), 8.22 (s, lH);Mass (m/z): 281.2 (M+H)+

The synthetic route of 106961-33-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUVEN LIFE SCIENCES LIMITED; WO2009/7995; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem