Pyridine-derivatives

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

Related Products of 10177-32-9, 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 10177-32-9 as follows.

MeI (0.2 mL, 3.00 mmol, 0.25 equiv) was added to a solution of methyl ester 14 (2 g, 12 mmol) in MeCN (16 mL), and the mixture was heated at 120 C under microwave conditions for 1 h. The solvent wasthen removed, and the oily residue was taken up in EtOAc, treated with charcoal, filtered, and re-concentrated to give 4-pyridinone 16 as a viscous oil that solidified to a near colourless solid on standing (2g, 95%). IR (ATR): 1645, 1717, 2950, 3013, 3053, 3094 cm-1. 1H NMR (CDCl3): delta = 8.12 (s, 1 H), 7.21-7.24 (dd, 3J = 7.7 Hz, 4J = 2.5 Hz,1 H), 6.44 (d, 3J = 7.5 Hz, 1 H), 3.83 (s, 3 H), 3.69 (s, 3 H). 13C NMR (CDCl3): delta = 174.8, 165.3, 146.6, 139.8, 122.7, 118.1, 51.9,44.9. HRMS (HESI): m/z [M + H]+ calcd for C8H9NO3: 168.0655; found:168.0657.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,10177-32-9, its application will become more common.

Reference:
Article; Koperniku, Ana; Zamiri, Maryam; Grierson, David S.; Synthesis; vol. 51; 8; (2019); p. 1779 – 1790;,
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 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

Reference of 845306-04-9, 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 845306-04-9, name is 6-Chloro-N-methylpicolinamide. This compound has unique chemical properties. The synthetic route is as follows.

A stirred solution of Intermediate 2 (0.6g, 1.91 mmol) in dry 1 ,4-dioxane (10 mL), was added cesium carbonate (1.9g, 5.88 mmol) followed by 6-chloro-N-methylpicolinamide (0.25 g, 1.47 mmol, ABCR). Nitrogen was flushed into the solution for 20 min and Pd(OAc)2 (0.016 g, 0.07 mmol) and 2-2′-bis (diphenylphosphino)-1,1′-binaphthyl (0.091 g, 0.14 mmol) were added. The reaction mixture was stirred at 100 C for 12 h. The resulting reaction mixture was filtered through celite and evaporated under vacuum. Water (5 mL) was added and the mixture was extracted with EtOAc (50mL). The organic layer was dried over anhydrous Na2SO4 and evaporated. The resulting crude product was purified by column chromatography ( brown solid). 1H NMR (400 MHz, DMSO-d6): delta 8.94-8.92 (m, 2H), 8.41 (d, J = 4.0 Hz, 1 H), 8.09 (d, J = 8.8 Hz, 1 H), 8.01 (s, 1 H), 7.94-7.94 (m, 1 H), 7.63 (t, J = 8.4 Hz, 1 H), 7.25-7.23 (m, 1 H), 6.94 (d, J = 8.4 Hz, 1 H), 3.79-3.77 (m, 1 H), 3.58-3.58 (m, 4H), 2.77 (d, J = 4.80 Hz, 3H), 2.59-2.58 (m, 2H), 2.49-2.45 (m, 2H), 1.45 (d, J = 6.80 Hz, 3H). LCMS: (Method A) 377.2 (M +H), Rt. 2.14min, 95.23% (Max). HPLC: (Method A) Rt. 2.07min, 96.75% (Max).

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 845306-04-9, 6-Chloro-N-methylpicolinamide.

Reference:
Patent; ASCENEURON S. A.; QUATTROPANI, Anna; KULKARNI, Santosh, S.; GIRI, Awadut Gajendra; (247 pag.)WO2017/144639; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 56673-34-8, Adding some certain compound to certain chemical reactions, such as: 56673-34-8, name is 3-Bromo-6-mercaptopyridine,molecular formula is C5H4BrNS, 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 56673-34-8.

To a solution of 5-bromopyridine-2-thiol (3.9 g) in THF (100 ml_) was added NaH (1 .24 g) at 0C and the mixture was stirred at 0C for 0.5 h. Then (bromomethyl)cyclopropane (2.79 g) was added. The mixture was allowed to warm to r.t. and stirred for 6 hours. Themixture was poured into ice water (200 ml_) and extracted with EA (100 ml_ x 3). The combined organic phases were washed with brine (50 ml_) and then dried over Na2SO4. After filtration and evaporation of the solvent, the residue was purified by SGC (eluent: PE) to provide the subtitle compound. MS ESI+: m/z = 244 [M+H]+.

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. 56673-34-8, 3-Bromo-6-mercaptopyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SANOFI; SCHWINK, Lothar; BOSSART, Martin; GLOMBIK, Heiner; GOSSEL, Matthias; KADEREIT, Dieter; KLABUNDE, Thomas; MAIER, Thomas; STENGELIN, Siegfried; WO2014/56938; (2014); 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

Reference of 19842-08-1, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 19842-08-1, name is 2-Bromo-5-ethylpyridine. A new synthetic method of this compound is introduced below.

To a stirred solution of 2-bromo-5-cyclopropylpyridine (1 g, 5 mmole) in CHC13(15 mL) was added mCPBA (1.7, 1.5 equiv). The reaction mixture was heated to 50 C. for 4 hours to complete the reaction. It was cooled and diluted with 20 mL DCM and washed with sat. NaHCO3 solution (5×15 mL) until no acid left in the organic layer. It was then dried by Na2SO4 and concentrated in vacuuo, which (Ig) was ready for the next step.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,19842-08-1, its application will become more common.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAK, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; (905 pag.)WO2017/35353; (2017); 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 132097-09-7, 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.132097-09-7, name is 2,4-Dichloro-3-methylpyridine, molecular formula is C6H5Cl2N, molecular weight is 162.02, as common compound, the synthetic route is as follows.

4-HYDROXY-PIPERIDINE-1-CARBOXYLIC acid isopropyl ester (0.496 mL, 2. 90 mmol) was dissolved in anhydrous DIMETHYLACETAMIDE (DMA, 5 mL), NaH (60% oil dispersion, 116 mg, 2.90 mmol) was added and this mixture was stirred at 23C for 45 min, then this mixture was added dropwise to 2,4- dichloro-3-methyl-pyridine, which was dissolved in anhydrous DMA (4 mL). This mixture was stirred at 23 OC for 2 h then heated at 50C for 15 h, after which time the mixture was diluted with ET20 (140 mL), washed with water (14 mL), then brine twice (2 x 14 mL). The organic layer was separated, dried with MGS04, and the solvent was evaporated in vacuo to give an oil which was purified by flash chromatography using hexanes-EtOAc, 75: 25, V/V, then hexanes-EtOAc, 50: 50, V/V, to give 4-(2-chloro-3-methyl-pyridin-4-yloxy)-piperidine-1-carboxylic acid isopropyl ester as a solid (223 mg, 27%). H NMR (CDC13, 400 MHz) No. 8.09 (d, 1H), 6.69 (d, 1H), 4.91 (M, 1H), 4. 60 (M, 1H), 3.61 (M, 2H), 3.52 (M, 2H), 2.24 (s, 3H), 1.91 (M, 2H), 1.80 (M, 2H), 1.24 d, 6H). LRMS calculated for C15H21CIN203 : 312.12, Found: (MH) + 313. 4.

The chemical industry reduces the impact on the environment during synthesis 132097-09-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; WO2005/7647; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem