Trichloroacetonitrile → 3-chloro-4-[(3,4-dimethoxyphenyl)methoxy]-N-methyl-N-[2-[[(1-methylethyl)amino]carbonyl]-4-phenoxyphenyl]-benzamide

Participants

Reaction Steps

A slurry of 1B (28 mg, 0.09 mmol) and trichloroacetonitrile (0.009 mL, 0.09 mmol) in CH2Cl2 (1 mL) at room temperature was treated with a solution of triphenylphosphine (22 mg, 0.09 mmol) in THF (0.25 mL). The reaction mixture was stirred for 30 minutes and additional trichloroacetonitrile (0.009 mL, 0.09 mmol) and triphenylphosphine (22 mg, 0.09 mmol) were added. The resulting solution was treated with 44B (16 mg, 0.06 mmol) in CH2Cl2 (0.5 mL). The stirring was continued for 2 hours, and then the reaction concentrated to dryness. The residue was purified by chromatography (SiO2, 50% to 75% EtOAc in hexanes) to afford 44C (31 mg).

Provenance & Evidence