Boron tribromide → HCID 66599603, compound

Participants

Reaction Steps

To a cooled (−78° C.) solution of [6-(4-Dimethylamino-piperidin-1-yl)-1H-benzoimidazol-2-yl]-(3-isoquinolin-4-yl-4-methoxy-phenyl)-methanone (6 mg, 0.012 mmol) in dichloromethane (6 mL) was added boron tribromide (0.118 mL, 10 eq) dropwise resulting in bright yellow solution. The reaction mixture was allowed to warm, diluted with saturated ammonium chloride solution, and extracted with dichloromethane. The organics were dried over Na2SO4, filtered, concentrated and purified by HPLC (Deltapak C18, acetonitrile: 0.1% trifluoroacetic acid), then neutralized using PL-HCO3 SPE to obtain 1 mg [6-(4-dimethylamino-piperidin-1-yl)-1H-benzoimidazol-2-yl]-(4-hydroxy-3-isoquinolin-4-yl-phenyl)-methanone in 20% yield. MS m/z 492.4 (M+H)+.

Provenance & Evidence