Cesium carbonate → 6-(3-Chloro-phenyl)-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

6-Chloro-5-(3,3-difluoroazetidin-1-yl)-pyridine-2-carboxylic acid methyl ester (Example 69 a, 0.3 g, 1.15 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride methylene chloride complex (CAN 72287-26-4, 47 mg, 0.058 mmol) and cesium carbonate (CAN 534-17-8, 0.56 g, 1.72 mmol) were added to a solution of 3-chlorophenylboronic acid (CAN 63503-60-6, 0.27 g, 1.72 mmol) in water (20 mL) and DMF (10 mL). The mixture was stirred for 48 h at 100° C. The reaction mixture was adjusted to pH=3 and extracted with methylene chloride (3×20 mL). The organic layers were combined, dried over sodium sulfate and concentrated to give the crude product (110 mg, 30%); MS (EI): 325.0 [M+H]+.

Provenance & Evidence