Reference of 1159812-31-3 , The common heterocyclic compound, 1159812-31-3, name is 7-Bromo-2-methyl-[1,2,4]triazolo[1,5-a]pyridine, molecular formula is C7H6BrN3, 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.
7-bromo-2-methyl-[l,2,4]triazolo[l,5-a]pyridine (50.9 mg, 0.240 mmol), potassium acetate (70.7 mg, 0.720 mmol), 2nd generation XPhos precatalyst (14.16 mg, 0.018 mmol) and bis(pinacolato)diboron (60.9 mg, 0.240 mmol) were added to a 40 mL reaction vial and evacuated and charged multiple times with nitrogen. Added dioxane (1920 mu), then evacuated and charged the vessel again with nitrogen (3x). Heated to 100C and monitored by LCMS for loss of bromopyrazole. Once bromopyrazole was consumed, the reaction was cooled to room temperature and 2-bromo-6-chloro-3-(l-((l-fluorocyclopentyl)methyl)-lH-pyrazol-4-yl)-5-methylpyridine (INTERMEDIATE H6, 89 mg, 0.240 mmol) was added along with l, l’-bis(di-tert- butylphosphino)ferrocene palladium dichloride (9.39 mg, 0.014 mmol). The reaction was evacuated and charged 3x with nitrogen, followed by the addition of 3M aqueous potassium carbonate (240 mu, 0.720 mmol). Heated to 50C overnight. Partitioned between water and ethyl acetate. Extracted the aqueous twice more with ethyl acetate. The organics were passed over a bed of sodium sulfate and the filtrate evaporated. Purified by silica gel chromatography, eluting with 20-100% 3 : 1 EtOAc:EtOH in hexanes to give the title compound. MS(M+1): 425.
The synthetic route of 1159812-31-3 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; MERCK SHARP & DOHME CORP.; MSD R&D (CHINA) CO., LTD.; ACTON, John, J., III; BAO, Jianming; DENG, Qiaolin; EGBERTSON, Melissa; FERGUSON, Ronald, III; GAO, Xiaolei; HARRISON, Scott Timothy; KNOWLES, Sandra, L.; LI, Chunsing; LO, Michael Man-Chu; MAZZOLA, Robert, D., Jr.; MENG, Zhaoyang; NA, Meng; RUDD, Michael, T.; SELYUTIN, Oleg, B.; TELLERS, David, M.; TONG, Ling; ZHANG, Fengqi; (195 pag.)WO2019/5587; (2019); A1;,
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