Tricyclohexylphosphine → (3-chloro-5-oxo-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-7-yl)boronic acid

Participants

Reaction Conditions

Reaction Steps

7-bromo-3-chloro-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-5-one (1.00 g, 3.12 mmol), Pd2(dba)3 (0.146 g, 0.16 mmol), tricyclohexylphosphine (0.104 g, 0.37 mmol), bis(pinacolato)diboron (0.87 g, 3.43 mmol) and potassium acetate (0.61 g, 6.23 mmol) were mixed in a dry flask through which argon was purged. The flask was charged with 40 mL of dry dioxane and argon was bubbled through the solution for 15 minutes. The reaction was heated to 95° C. and stirred under argon. After 6 h, the reaction mixture was poured into 500 mL of ethyl acetate and 100 mL of saturated aqueous ammonium chloride. The organic layer was separated, dried with magnesium sulfate, filtered, and concentrated to afford the title compound. LRMS (APCI) calculated for C14H10BClNO3 [M+H]+, 286.0; found 286.1.

Provenance & Evidence