Hydrochloric Acid → HCID 89579710, compound

Participants

Reaction Conditions

Reaction Steps

A 100 mL round bottom flask was charged with 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)-2-(trifluoromethyl)benzonitrile (1.5 g, 3.86 mmol), 2-chloro-6-vinylpyrimidine-4-carboxylic acid (709.5 mg, 3.86 mmol), PdCl2(PPh3)2 (190 mg, 0.27 mmol), and cesium carbonate (2.5 g, 7.72 mmol) in DME (8 mL), EtOH (4 mL), and water (8 mL). The reaction mixture was heated to 90° C. for 10 hours. The reaction mixture was diluted with 100 mL water, acidified to pH 5 with aqueous 4N HCl, and extracted with 2×100 mL EtOAc. The combined organic layers were dried over sodium sulfate and concentrated to give 2-(4-(4-cyano-3-(trifluoromethyl)phenoxy)phenyl)-6-vinylpyrimidine-4-carboxylic acid as a light brown solid. The material was used in the next step without purification. LC/MS: m/z=412 [M+H]+.

Provenance & Evidence