Sodium Hydroxide → HCID 86718794, compound

Participants

Reaction Steps

To a yellow solution of trimethylsulfoxonium iodide (1.31 g, 5.97 mmol) in DMSO (31.8 mL) under nitrogen at rt was added sodium hydride (0.239 g, 5.97 mmol). The color disappeared and bubbling occurred. Stirring was continued at rt for 30 min, and then a solution containing a mixture of 4-chloro-1-{[(1S)-3-oxocyclohexyl]methyl}-1H-benzimidazole-6-carbonitrile (1.15 g, 3.98 mmol) and (3S)-3-[(6-bromo-4-chloro-1H-benzimidazol-1-yl)methyl]cyclohexanone (1.36 g, 3.98 mmol) dissolved in DMSO (7.96 mL) was slowly added. After stirring 16 h, brine solution (25 mL) was added followed by 2 N NaOH (25 mL) to pH 13. The product was extracted into EtOAc (3×75 mL). The combined organics were washed with water (2×150 mL), dried over Na2SO4, filtered, and concentrated onto florisil for purification on a 12 g silica gel column (0-2% MeOH/DCM, 20 min gradient; 30 mL/min elution; 254 nm detection) to afford the title compound (0.735 g, 55% yield). MS (m/z) 302.1 (M+H+).

Provenance & Evidence