Tag: M.W:200-300

Electric Literature of 386704-06-9 , The common heterocyclic compound, 386704-06-9, name is 2-Chloro-6-(trifluoromethyl)nicotinonitrile, molecular formula is C7H2ClF3N2, 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.

2-Chloro-6-(trifluoromethyl)nicotinonitrile (340 mg, 1.65 mmol) was diluted with toluene (2.0 rnL), placed under nitrogen and cooled to -78C. DIBAL-H (3292 mul, 3.29 mmol) was added dropwise and the reaction was stirred for 1 hour. The reaction was warmed to 00C and acetic acid (1 mL) was added followed by 5 mL of water. After stirring for 2 hours, the reaction was extracted twice with ethyl acetate, washed with Rochelle’s salt, dried over MgSO4, filtered and concentrated. The material was loaded onto silica gel and eluted with 5% ethyl acetate/hexanes to 30% ethyl acetate/hexanes to yield the desired compound(115 mg, 0.549 mmol, 33.3 % yield) as a clear oil.

The synthetic route of 386704-06-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARRAY BIOPHARMA INC.; COOK, Adam; HUNT, Kevin, W.; DELISLE, Robert Kirk; ROMOFF, Todd; CLARK, Christopher, T.; KIM, Ganghyeok; CORRETTE, Christopher, P.; DOHERTY, George, A.; BURGESS, Laurence, E.; WO2010/75200; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1227573-02-5, 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.1227573-02-5, name is 3-Bromo-5-fluoroisonicotinaldehyde, molecular formula is C6H3BrFNO, molecular weight is 204, as common compound, the synthetic route is as follows.

To a solution of 3-bromo-5-fluoroisonicotinaldehyde (5.0 g, 24.5 mmol, 1.0 eq) in DME (25.0 mL) was added Eta2 Eta220 (25.0 mL) and the reaction mixture was heated at 110 C overnight. After the reaction was complete, the solvent was concentrated. The resulting residue was diluted by water, extracted by EA (100.0 mL X 3), washed by brine, dried over Na2S04, concentrated. The resulting residue was purified by column chromatography (PE: EA = 2: 1) to provide 4-bromo-lH-pyrazolo[3,4-c]pyridine (1.5 g, 31.3%) as a white solid. LCMS (M+H+) m/z calculated 198.1, found 198.2.

The chemical industry reduces the impact on the environment during synthesis 1227573-02-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; LIFESCI PHARMACEUTICALS, INC.; MCDONALD, Andrew; QIAN, Shawn; (346 pag.)WO2018/11628; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 122851-69-8, 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.122851-69-8, name is 3-Bromo-2-(chloromethyl)pyridine, molecular formula is C6H5BrClN, molecular weight is 206.47, as common compound, the synthetic route is as follows.

A solution of cis-4-(2,6-difluorophenyl)cyclohexanol (2.69 g) in THF (60 ml) wascooled to 0C, 60% sodium hydride (1.014 g) was added, and the mixture was stirredunder a calcium chloride tube dry atmosphere for 2 hr. To the reaction mixture wasadded 3-bromo-2-(chloromethyl)pyridine (3.40 g), and the mixture was stirred at roomtemperature for 30 min, and at 70C overnight. Water was added to the mixture atroom temperature, and the mixture was extracted with ethyl acetate. The organic layerwas washed with water and saturated brine, dried over anhydrous magnesium sulfate,and the solvent was evaporated under reduced pressure. The residue was purified bysilica gel chromatography (ethyl acetate/hexane) to give the title compound (3.96 g).MS, found: 382.0,384.0.

Statistics shows that 122851-69-8 is playing an increasingly important role. we look forward to future research findings about 3-Bromo-2-(chloromethyl)pyridine.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; FUJIMOTO Tatsuhiko; RIKIMARU Kentaro; FUKUDA Koichiro; SUGIMOTO Hiromichi; MATSUMOTO Takahiro; TOKUNAGA Norihito; HIROZANE Mariko; (166 pag.)WO2017/135306; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 54718-39-7, 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 54718-39-7, name is 2,5,6-Trichloronicotinic acid. This compound has unique chemical properties. The synthetic route is as follows.

1,1′-Carbonyldiimidazole (40 g, 247 mmol) was added in portions to 2,5,6-trichloronicotinic acid (50.7 g, 224 mmol, Combi-Blocks, San Diego, Calif., USA) in THF (400 mL), allowing gas evolution to cease between additions. The resulting mixture was stirred for 5 min and then was degassed with house vacuum and flushed with nitrogen (*2). The resulting mixture was heated to 50 C. for 60 min, then diluted with toluene (100 mL) and concentrated to half volume. The resulting mixture was cooled to 0 C. and ammonium hydroxide (60 mL, 437 mmol) was added slowly via syringe. The reaction was stirred for 10 min at room temperature, diluted with EtOAc (200 mL) and washed with water (3*100 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated. The residue was suspended in 9:1 heptane/EtOAc (300 mL) and filtered. The filtered solids were collected and the remaining mother liquor was partially evaporated to half volume, cooled to 0 C., and filtered. The two crops of filtered solids were combined to provide 2,5,6-trichloronicotinamide (Intermediate P, 46.2 g, 92% yield).

According to the analysis of related databases, 54718-39-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Amgen Inc.; ALLEN, John Gordon; LANMAN, Brian Alan; CHEN, Jian; REED, Anthony B.; CEE, Victor J.; LIU, Longbin; LOPEZ, Patricia; WURZ, Ryan Paul; NGUYEN, Thomas T.; Booker, Shon; ALLEN, Jennifer Rebecca; CHU-MOYER, Margaret; AMEGADZIE, Albert; CHEN, Ning; GOODMAN, Clifford; LOW, Jonathan D.; MA, Vu Van; MINATTI, Ana Elena; NISHIMURA, Nobuko; PICKRELL, Alexander J.; WANG, Hui-Ling; SHIN, Youngsook; SIEGMUND, Aaron C.; YANG, Kevin C.; TAMAYO, Nuria A.; WALTON, Mary; XUE, Qiufen; US2019/374542; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 186413-75-2, name is 3-Bromo-6-chloro-2-methyl-5-nitropyridine, the common compound, a new synthetic route is introduced below. Product Details of 186413-75-2

Intermediate 4: S-Bromo-l-chloro–methyl-pyridin-S-ylamine In a 250ml RB flask, 3-bromo-6-chloro-2-methyl-5-nitropyridine (1.5 g, 5.97 mmol, commerical) was dissolved in ethyl acetate (20 mL). To this solution, ammonium chloride (3.19 g, 59.65 mmol) dissolved in water (10ml) was added and stirred at RT for 10 minutes. Then zinc powder (2.340 g, 35.79 mmol) was added at once and the resulting reaction mixture was refluxed at 550C for 6hrs. The reaction mixture was filtered through ceilite and concentrated in vacuo. The residue was partitioned between ethyl acetate (150ml) and water (75). The organic layer was dried over anhydrous sodium sulphate and concentrated in vacuo. The crude product was purified by Flash column chromatography using Argonaut purification system, which was eluted with 12% ethyl acetate in hexane to give 5-bromo-2-chloro-6-methylpyridin-3-amine (0.500 g, 37.8 %) as white solid. MS (ES+): 222 for C6H6BrClN2

The synthetic route of 186413-75-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/147431; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1167056-96-3, Adding some certain compound to certain chemical reactions, such as: 1167056-96-3, name is 3-Bromo-5-chloro-1H-pyrrolo[2,3-c]pyridine,molecular formula is C7H4BrClN2, 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 1167056-96-3.

To a stirred solution of 3-bromo-5-chloro- 1H- pyrrolo[2,3-c]pyridine (AJ-2) (2.9 g, 12.6 mmol) in anhydrous DMF (100 mL) was added 2- chloro-6-(trifluoromethyl)benzoyl chloride (4.6 g, 18.9 mmol) and NaH (60%) (1 g, 25.2 mmol). The solution was stirred at r.t for 2 hours. The solution was quenched with H20 (400 mL). The suspension was extracted with EtOAc (150 mL x 3). The combined organic layer was washed with H20 (100 mL x 2) and brine (100 mL x 2) and dried over anhydrous Na2S04. The solution was evaporated and dried over vacuo and 5.7 g product was obtained. LCMS (ESI) calc’d for Ci5H6BrCl2F3N20 [M+H]+: 437, found: 437.

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. 1167056-96-3, 3-Bromo-5-chloro-1H-pyrrolo[2,3-c]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BARR, Kenneth Jay; BEINSTOCK, Corey; MACLEAN, John; ZHANG, Hongjun; BERESIS, Richard Thomas; ZHANG, Dongshan; WO2014/26327; (2014); 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. 23056-47-5, name is 2-Bromo-4-methyl-5-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 23056-47-5

To a solutionof 2-bromo-4-methyl-5-nitropyridine (5.00 g, 23.0 mmol) in tetrahydrofuran (THF)(30 ml) was added Raney nickel (slurry in water). The reaction mixture washydrogenated (balloon) overnight at room temperature. The mixture was filteredthrough Celite, and concentrated under reduced pressure. The residue waspurified by silica gel column chromatography (0-50% EtOAc in hexanes) to afford27 as a yellow solid (4.02 g, 93%yield).1H NMR (300 MHz, CDCl3): delta ppm2.15 (d, J = 0.9 Hz, 3 H), 7.14 (s, 1 H), 7.78 (s, 1 H).

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, 23056-47-5, 2-Bromo-4-methyl-5-nitropyridine.

Reference:
Article; Matsuda, Daisuke; Kobashi, Yohei; Mikami, Ayako; Kawamura, Madoka; Shiozawa, Fumiyasu; Kawabe, Kenichi; Hamada, Makoto; Oda, Koji; Nishimoto, Shinichi; Kimura, Kayo; Miyoshi, Masako; Takayama, Noriko; Kakinuma, Hiroyuki; Ohtake, Norikazu; Bioorganic and Medicinal Chemistry Letters; vol. 26; 15; (2016); p. 3441 – 3446;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 58483-98-0, 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.58483-98-0, name is 2-Amino-5-bromonicotinamide, molecular formula is C6H6BrN3O, molecular weight is 216.04, as common compound, the synthetic route is as follows.

A mixture of 2-amino-5-bromonicotinamide (100 mg, 0.46 mmol), 3-fluorobenzaldehyde (69 mg, 0.56 mmol), NaHSO3 (40 mg, 0.38 mmol), 4-methylbenzene sulfonicacid (15 mg, 0.05 mmol) in DMAc (3 mL) was stirred at 115C for 1.5 h, then additional NaHSO3(40 mg, 0.38 mmol) was added to the mixture. After 1.5 h, the third portion of NaHSO3 (40 mg,0.38 mmol) was added to the mixture. After being stirred overnight at 115C, the reaction mixturewas concentrated in vacuo, suspended in water and filtered to give the product of 6-bromo-2-(3-fluorophenyl)pyrido[2,3-d]pyrimidin-4(3H)-one (70 mg, yield: 47%), which was used for the nextstep without further purification. ?H-NMR (DMSO-d6, 400 MHz) 13.04 (br s, 1H), 9.07 (d, J2.8 Hz, 1H), 8.65 (d, J= 2.8 Hz, 1H), 8.08 (d, J= 8.0 Hz, 1H), 8.02 (dd, J= 9.6, 1.6 Hz, 1H), 7.607.68 (m, 1H), 7.457.54 (m, 1H). MS (M+H): 320/322.

Statistics shows that 58483-98-0 is playing an increasingly important role. we look forward to future research findings about 2-Amino-5-bromonicotinamide.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DAI, Xing; LIU, Hong; PALANI, Anandan; HE, Shuwen; NARGUND, Ravi; XIAO, Dong; ZORN, Nicolas; DANG, Qun; MCCOMAS, Casey C.; PENG, Xuanjia; LI, Peng; SOLL, Richard; WO2014/205593; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 116026-95-0, name is tert-Butyl (4-formylpyridin-3-yl)carbamate, the common compound, a new synthetic route is introduced below. Application In Synthesis of tert-Butyl (4-formylpyridin-3-yl)carbamate

Sodium triacetoxyborohydride (0.57 g, 2.70 mmol) and acetic acid (0.41, 6.75 mmol) were added to a solution OF N-BOC-3-AMINO-4-PYRIDINE carboxaldehyde (0.50 g, 2.25 mmol) and ETHYL 4-AMINOPIPERIDINE-1-CARBOXYLATE (0.47 g, 2.70 mmol) in dichloroethane (5 rriL) at room temperature. The reaction was stirred overnight, and quenched with saturated aqueous sodium bicarbonate. This was separated, extracted with ethyl acetate and the combined organics were dried over sodium sulfate. The solution was filtered and evaporated to give the crude product. This was purified by chromatography (silica GEL, 1 to 12% methanol in methylene chloride gradient elution), which gave the title compound (0.47 g). MS 379.3.

The synthetic route of 116026-95-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2004/92166; (2004); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 623942-84-7, 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.623942-84-7, name is (3-Bromo-6-methoxypyridin-2-yl)methanol, molecular formula is C7H8BrNO2, molecular weight is 218.05, as common compound, the synthetic route is as follows.

(3-bromo-6-methoxypyridin-2-yl)methanol (2.5 g, 11.4 mmol) and CBr4 (4.5 g, 13.6 mmol) were added into DCM (30 mL). PPh3 (3.6 g, 13.6 mmol) in DCM (10 mL) was added dropwise into the reaction mixture at 0 C. The mixture was stirred at 0 C for 0.5 hour. The reaction was concentrated to give a residue. The residue was purified by flash silica gel chromatography (40 g column, EtOAc in petroleum ether from 0% to 10%) to afford 3- bromo-2-(bromomethyl)-6-methoxypyridine (2.69 g, 84% yield) as a colorless oil. LCMS m/z [M+H]+ = 281.8.

Statistics shows that 623942-84-7 is playing an increasingly important role. we look forward to future research findings about (3-Bromo-6-methoxypyridin-2-yl)methanol.

Reference:
Patent; RELAY THERAPEUTICS, INC.; D.E. SHAW RESEARCH, LLC; TAYLOR, Alexander, M.; LESCARBEAU, Andre; KELLEY, Elizabeth, H.; SHORTSLEEVES, Kelley, C.; WALTERS, W., Patrick; MURCKO, Mark, Andrew; MCLEAN, Thomas, H.; GUNAYDIN, Hakan; GIORDANETTO, Fabrizio; THERRIEN, Eric; (607 pag.)WO2019/183367; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem