Synthetic Route of 52311-50-9 ,Some common heterocyclic compound, 52311-50-9, molecular formula is C7H8ClNO, 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 degassed mixture of 4-(4,4,5,5-tetramethyl-l ,3,2-dioxaborolan-2- yl)benzamide ( 9.4g, 38 mmol) and 2-chloro-4-ethoxypyridine ( 5g, 31.7 mmol) in dioxane was added Brettphos-prePd (catalytic amount) and CS2CO3 (12.3 g, 37.8 mmol) under N2atmosphere. The mixture was heated to 100 C and stirred for 3.5 hours. The reaction mixture was cooled to room temperature and filtered. The filtrate was concentrated, and the residue was purified on silic-gel (PE: EA = 100% ~ 30%) to give N-(4-ethoxypyridin-2-yl)-4-(4,4,5,5-tetramethyl-l ,3,2-dioxaborolan-2-yl)benzamide (8.8 g, yield 75%). 1HNMR (400MHz, CDC13): 5=8.74 (s, 1 H), 8.05~8.02(m, 1 H), 8.01 (s, 1 H), 7.94-7.89 (m, 4 H), 6.60-6.59 (m, 1 H), 4.20-4.14 (m, 2 H), 1.47-1.43 (m, 3 H), 1.36 (s,12 H), MS (ESI):M/Z (M+l)=369.19.
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. 52311-50-9, 2-Chloro-4-ethoxypyridine, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; MERCK SHARP & DOHME CORP.; WU, Hao; KIM, Ronald M.; LIU, Jian; GAO, Xiaolei; BOGA, Sobhana Babu; GUIADEEN, Deodialsingh; KOZLOWSKI, Joseph; YU, Wensheng; ANAND, Rajan; YU, Younong; SELYUTIN, Oleg B.; GAO, Ying-Duo; LIU, Shilan; YANG, Chundao; WANG, Hongjian; WO2014/114185; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem