Hydrochloric Acid → 4-(6-Carbamoyl-3,5-dimethylpyrazin-2-yl)phenylboronic acid

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Reaction Steps

Sodium periodate (19.64 g, 91.81 mmol) was added in one portion to 3,5-dimethyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrazine-2-carboxamide (Intermediate 7-6; 10.81 g, 30.60 mmol) in THF (320 mL) and water (80 mL) and the resulting cloudy suspension was stirred at ambient temperature for 30 minutes. 1M hydrochloric acid (21.42 mL, 21.42 mmol) was added and the resulting suspension was stirred at ambient temperature for 17 hours. The reaction mixture was evaporated and diluted with water (100 mL) and the precipitate was collected by filtration, washed with water (400 mL) and dried under vacuum at 65° C. over 4 hours to afford 4-(6-carbamoyl-3,5-dimethylpyrazin-2-yl)phenylboronic acid (7.13 g, 86%) as a white solid, which was used without further purification.

Provenance & Evidence