Tag: M.W:200-300

Synthetic Route of 17282-03-0 ,Some common heterocyclic compound, 17282-03-0, molecular formula is C6H5BrClN, 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.

3-Bromo-2-ethoxy-5-methylpyridine To a solution of 3-bromo-2-chloro-5-methylpyridine (4.00 g, 19.37 mmol) in ethanol (100 mL) was added sodium ethoxide (6.59 g, 96.9 mmol) in three portions. The mixture was stirred under nitrogen at 100 C. for 2 days. The reaction was cooled to room temperature, diluted with water and extracted with DCM. The combined organic layers were dried (Na2SO4), and the solvent was removed under reduced pressure. Purification (FCC, SiO2, 20%, EtOAc/hexanes) afforded the title compound (3.00 g, 72%). 1H NMR (400 MHz, DMSO-d6) delta 7.94 (dd, J=0.8, 2.3 Hz, 1H), 7.89-7.82 (m, 1H), 4.31 (q, J=7.0 Hz, 2H), 2.18 (t, J=0.8 Hz, 3H), 1.30 (t, J=7.0 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,17282-03-0, its application will become more common.

Reference:
Patent; Bollu, Venkataiah; Breitenbucher, James; Kaplan, Alan; Lemus, Robert; Lindstrom, Andrew; Vickers, Troy; Wilson, Mark E.; Zapf, James; US2014/275531; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 77837-08-2 ,Some common heterocyclic compound, 77837-08-2, molecular formula is C12H9NO3, 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.

d2-5-(Hydroxymethyl)-1-phenylpyridine-2(1H)-one: Isobutyl chloroformate (0.45 mL, 3.49 mmol) was added to a solution of 6-oxo-1-phenyl-1,6-dihydropyridine-3-carboxylic acid (0.500 g, 2.32 mmol) and N-methylmorpholine (0.38 mL, 3.49 mmol) in tetrahydrofuran (10 mL) at -5° C. The mixture was stirred for 3 hours at the same temperature, diluted with tetrahydrofuran and filtered over a pad of Celite under argon. The filtrate containing the mixed anhydride was added dropwise to a suspension of sodium borodeuteride (0.117 g, 2.79 mmol) in tetrahydrofuran at -10° C. The reaction mixture was allowed to warm to room temperature and stirred for 16 hours, after which D2O (1 mL) was added. Standard extractive work up gave a crude residue which was purified by preparative HPLC to give the title compound as a white solid (0.290 g, 61percent). m.p. 115-120° C.; 1H NMR (400 MHz, CDCl3) delta 2.05 (br, 1H), 6.66 (d, J=9.1 Hz, 1H), 7.25-7.51 (m, 7H); IR (KBr) nu 3337, 1665, 1586, 1535, 1257 cm-1; MS 204 (M+1).

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. 77837-08-2, 6-Oxo-1-phenyl-1,6-dihydropyridine-3-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AUSPEX PHARMACEUTICALS, INC.; US2008/319026; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 59352-90-8, 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 59352-90-8 as follows.

The mixture of 5-bromo-6-methylpyridine-2,3-diamine (500.0 mg, 2.47 mmol) and diethyloxalate (3.0 mL) was stirred at 100° C. for 12 hours and then cooled to room temperature. Et2O was added to the reaction mixture to form a solid. The formed solid was then filtered and dried under reduced pressure to obtain light brown solid compound of 7-bromo-6-methylpyrido[2,3-b]pyrazine-2,3-diol (611.0 mg, 97percent). [1093] LCMS ESI (+): 256 (M+1), 258 (M+3) [1094] 1H-NMR (400 MHz, DMSO-d6); delta: 12.40 (s, 1H), 11.94 (s, 1H), 7.53 (s, 1H), 2.48 (s, 3H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,59352-90-8, its application will become more common.

Reference:
Patent; C&C RESEARCH LABORATORIES; Ho, Pil Su; Yoon, Dong Oh; Han, Sun Young; Lee, Won Il; Kim, Jung Sook; Park, Woul Seong; Ahn, Sung Oh; Kim, Hye Jung; US2014/315888; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 951626-91-8, 5-Bromo-3-chloro-1H-pyrrolo[2,3-b]pyridine, 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, 951626-91-8, blongs to pyridine-derivatives compound. Recommanded Product: 951626-91-8

Step 1: 3-chloro-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-pyrrolo[2,3-b]pyridine To a solution of 5-bromo-3-chloro-lH-pyrrolo[2,3-b]pyridine (1.0 g, 4.32mmol) in 1,4-dioxane (20 mL) was added 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(l,3,2-dioxaborolane) (1.32 g, 5.18 mmol), potassium acetate (1.27 g, 12.96 mmol) and l,l’-bis(diphenylphosphino)ferrocene- palladium(II)dichloride (315 mg, 0.43 mmol). The reaction mixture was purged with nitrogen for 2 min and heated to 100 C for 2 h and subsequently concentrated to dryness in vacuo. The resulting viscous mass was diluted with water and extracted with ethyl acetate (2 x 50 mL). The combined organic layers were dried over sodium sulfate and concentrated to dryness in vacuo. The resulting residue was purified by column chromatography (silica gel, 100-200 mesh, 30% ethyl acetate in petroleum ether ) affording 3-chloro-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-pyrrolo[2,3- bjpyridine (770 mg, 64%): lU NMR (400 MHz, Chloroform-d) delta 11.61 (s, 1H), 8.76 (s, 1H), 8.45 (s, 1H), 7.33 (s, 1H), 1.40 (s, 12H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,951626-91-8, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; ESTRADA, Anthony; HUESTIS, Malcolm; KELLAR, Terry; PATEL, Snahel; SHORE, Daniel; SIU, Michael; (260 pag.)WO2016/142310; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 153034-78-7, 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 153034-78-7, name is 2-Fluoro-3-iodo-5-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

In a 20-ml flask, 2-fluoro-3-iodo-5-methylpyridine (1.0 g, 4.2 mmol), potassium acetate (828 mg, 8.4 mmol), acetic acid (1 ml) and aniline (393 mg, 4.2 mmol) were mixed, and the solution was heated to reflux for 10 hours. After allowing the solution to stand overnight at room temperature, aniline (393 mg, 4.2 mmol) was added, and the mixture was further heated to reflux for 10 hours. After allowing the mixture again to stand overnight at room temperature, aniline (393 mg, 4.2 mmol) was added, and the mixture was further heated to reflux for 8 hours. This reaction solution was cooled to room temperature, ethyl acetate (20 ml) was added thereto. The organic layer was separated and washed with water (5 ml) two times. The organic layer was washed twice with a saturated aqueous sodium bicarbonate solution (10 ml) and further washed with saturated brine (10 ml) . The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure, diisopropyl ether (about 50 ml) was added to the residue, and a precipitate was filtered off. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (hexane : ethyl acetate = 4:1). The obtained extract was concentrated under reduced pressure, and dried under reduced pressure at 50C, to yield the title compound (539 mg, 1.7 mmol) as a yellow oily material (yield 41.2%) . 1H-NMR (CDCl3, TMS, 300 MHz) delta (ppm) : 2.17 (s, 3H), 6.77 (brs, IH), 6.98-7.03 (m, IH), 7.28-7.34 (m, 2H), 7.53-7.57 (m, 2H), 7.77-7.79 (s, 2H), 7.96-7.97 (m, IH).13C-NMR (CDCl3, TMS, 300 MHz) delta (ppm) : 17 . 04 , 81 . 16, 119.57 , 122 .48 , 125.72 , 128. 99, 140. 60, 147 .20, 147 .93, 151 . 92 High resolution mass spectrometry (Ci2HiIlN2 )Theoretical value : 308 .9889 [M-H] + Measured value : 309. 9892 [M-H] +

According to the analysis of related databases, 153034-78-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2008/16184; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 918516-27-5, 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.918516-27-5, name is 5-(4-Chlorophenyl)-1H-pyrrolo[2,3-b]pyridine, molecular formula is C13H9ClN2, molecular weight is 228.68, as common compound, the synthetic route is as follows.

To a suspension of 5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine (6b) (100 mg, 0.44 mmol) and N-(2,4-difluoro-3-formylphenyl)propane-1-sulfonamide (5) (139 mg, 0.53 mmol) in methanol (7.0 mL) was added potassium hydroxide (197 mg, 3.5 mmol). The reaction mixture was stirred at room temperature for 3 d and then evaporated to dryness. The crude reaction mixture was diluted with water (5.0 mL) and the pH adjusted to 7 with 4.0 N hydrochloric acid (10 mL). The resulting mixture was then diluted with water (25 mL) and extracted with ethyl acetate (3 x 20 mL). The combined organic layers were dried over sodium sulphate and evaporated in vacuo to give a crude solid (as a 2:1 mixture of the -OMe and free-OH 7b).

The chemical industry reduces the impact on the environment during synthesis 918516-27-5, I believe this compound will play a more active role in future production and life.

Reference:
Article; Buck, Jason R.; Saleh, Sam; Imam Uddin, Md.; Manning, H. Charles; Tetrahedron Letters; vol. 53; 32; (2012); p. 4161 – 4165;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 90902-84-4, 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. 90902-84-4, name is 2,5-Dibromopyridin-3-amine, molecular formula is C5H4Br2N2, 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.

(c) 1,1-Dimethylethyl (7-bromo-2-oxo-l,2,3,4-tetrahydro-l,5-naphthyridin-3- yl)carbamate; Zinc powder (0.934 g, 14.28 mmol) and iodine (0.054 g, 0.214 mmol) were heated in an evacuated flask which was then flushed with nitrogen 3 times. Methyl N- {[(l,l-dimethylethyl)oxy]carbonyl}-3-iodo-D-alaninate (2.35 g, 7.14 mmol, Aldrich Chemicals ) was dissolved in dry DMF (11.74 mL) and transferred via syringe to the reaction mixture which was previously cooled to 00C (reaction complete after 1.5h). The ice bath was removed and 2,5-dibromo-3-pyridinamine (2.392 g, 9.50 mmol) was added followed by bis (triphenylphosphine)palladium(II) chloride (0.251 g, 0.357 mmol) and the mixture heated at 40 0C for 14h. The mixture was cooled down and filtered through Celite, washing with EtOAc. Solvent was removed in vacuum. The mixture was redisolved in DMF (10 mL) and potassium carbonate (1.283 g, 9.28 mmol) was added. The resulting mixture was stirred at 80 0C for 6h. The mixture was concentrated and diluted with EtOAc, washed with water and brine and dried over Mg2SO4. Solvent was removed and the mixture chromatographed on silica eluting with 0-100% EtOAc :hexane to give the title compound (1.8 g, 5.26 mmol, 73.7 % yield) as light yellow solid. MS (ES+) m/z 343(MH+).

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 90902-84-4, 2,5-Dibromopyridin-3-amine.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/128961; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.105752-11-2, name is 3-Amino-4-iodopyridine, molecular formula is C5H5IN2, molecular weight is 220.0111, as common compound, the synthetic route is as follows.name: 3-Amino-4-iodopyridine

Step 1: 4-[(2-fluorophenyl)ethvnyl]pyridin-3-amineTo a solution of 3-amino-4-iodopyridine in Dioxane/DMF (1 :1, 0.7M) were sequentially added NEt3 (5eq.), CuI (0.04 eq.), trans-bis(triphenylphosphine) palladium(II) chloride (0.02 eq.) and l-ethynyl-2-fluorobenzene (2 eq.). After heating for 1 h at 70 0C, water was added and the mixture was extracted with Et2O. The combined organic layers were washed with brine, dried over Na2SO4, filtered and the solvent was evaporated in vacuo. The residue was purified by chromatography on silica gel, eluting with PE/EtOAc (50:50), affording the title compound(80%) as a solid. 1H NMR (400 MHz, OMSO-d6 + TFA, 300K) delta, 7.26-7.33 (dd, 2H, J = 7.6 Hz, J= 8 Hz), 7.52-7.53 (m, IH), 7.78 (d, IH, J= 8 Hz), 7.83 (t, IH, J= 6.4 Hz), 7.7 (d, IH, J= 5.6 Hz), 8.21 (s, IH); MS (ES+) m/z 213 (M +H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,105752-11-2, 3-Amino-4-iodopyridine, and friends who are interested can also refer to it.

Reference:
Patent; ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P. ANGELETTI S.P.A.; NARJES, Frank; HABERMANN, Jorg; COLARUSSO, Stefania; WO2010/115901; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1196155-38-0, 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. 1196155-38-0, name is 2-Chloro-6-(trifluoromethyl)isonicotinonitrile, molecular formula is C7H2ClF3N2, 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.

To a stirred solution of methyl 3,5-dihydroxybenzoate 2 (163 mg, 0.97 mmol) in DMF (10 mL) at RT, were added K2C03 (161 mg, 1.16 mmol) and 2-chloro-6- (trifluoromethyl)isonicotinonitrile 1 (200 mg, 0.97 mmol). The reaction mixture was stirred at RT for 16 h. The mixture was quenched with water (20 mL) and extracted with EtOAc (2 x 20 mL), and the combined organic extracts were washed with brine (10 mL), dried (Na2S04), filtered and concentrated. The residue was purified (silica gel; eluting 20-25percent EtOAc/hexanes) to afford compound 3 (110 mg, 34percent) as a white solid. 1H NMR (500MHz, CDC13): delta 7.59 (s, 1H), 7.41 – 7.44 (m, 2H), 7.36 (s, 1H), 6.90 (br s, 1H), 3.91 (s, 3H); LCMS Mass: 339.1 (M++l).

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 1196155-38-0, 2-Chloro-6-(trifluoromethyl)isonicotinonitrile.

Reference:
Patent; PHARMAKEA, INC.; ROWBOTTOM, Martin W.; HUTCHINSON, John Howard; CALDERON, Imelda; (202 pag.)WO2016/144703; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 66572-56-3, 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 66572-56-3, name is 2-Bromoisonicotinic acid. This compound has unique chemical properties. The synthetic route is as follows.

2-Bromoisonicotinic acid (2.02 g, 10 mmol) was dissolved in DMF (80 mL) under argon. Pd(PPh3)4 (0.6 g, 0.52 mmol) was added, and the reaction mixture was stirred at room temperature for 15 min. Na2CO3 (aq. 2N, 40 mL) was then added, followed by the addition of phenylboronic acid (1.67 g, 13.7 mmol). The reaction mixture was heated at 95C (18 h), cooled to room temperature and filtered through a celite pad. Water (80 mL) was added, and the mixture was acidified with HCl (2 N) to pH = 4. The precipitate was collected via filtration and rinsed with water (2 x 7 mL). The crude product was recrystallized from 2-methoxylethanol to give 2- phenylisonicotinic acid as a grey solid (1.2 g). 1HNMR (DMSO-d6, 400 MHz): delta 7.51 (m, 3H), 7.78 (d, J=4.8 Hz, 1H), 8.13 (t, J=1.6 Hz, 2H), 8.29 (s, 1H), 8.85 (d, j=4.8 Hz, 1H), 13.73 (bs, 1H).

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 66572-56-3, 2-Bromoisonicotinic acid.

Reference:
Patent; SIRTRIS PHARMACEUTICALS, INC.; WO2008/156869; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem