Ethanol → HCID 136160552, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 6-chloro-3,5-dimethylpyrazine-2-carboxamide (Intermediate A) (492 mg, 2.65 mmol) and 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (Intermediate 6-6; 630 mg, 2.65 mmol) and potassium phosphate, tri-basic (674 mg, 3.18 mmol) in DME (10 mL), ethanol (5 mL) and water (2.5 mL) was thoughroughly degassed. The mixture was treated with PdCl2(dppf)-DCM adduct (108 mg, 0.13 mmol), degassed again and the atmosphere replaced with nitrogen before being heated to 80° C. for 4 hours. The reaction mixture was allowed to cool to room temperature and then evaporated. The crude product was partitioned between EtOAc (75 mL), and 1N citric acid (25 mL) and the precipitate was collected by filtration, washed with water (10 mL) and air dried to afford 6-(3-fluoro-4-hydroxyphenyl)-3,5-dimethylpyrazine-2-carboxamide (481 mg, 69.6%) as a beige solid, which was used without further purification.

Provenance & Evidence