4-Isocyanato-1,2-dimethoxybenzene → HCID 86679582, compound

Participants

Reaction Steps

To a stirred suspension of (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-hydroxyethyl)pyridine 1-oxide (200 mg, 0.476 mmol) in anhydrous DCM (10 ml), a solution of DMAP (87 mg, 0.714 mmol) and 4-isocyanato-1,2-dimethoxybenzene (171 mg, 0.952 mmol) in anhydrous DCM (5 ml) was added dropwise within 10 minutes. The reaction mixture was stirred at RT overnight. After 18 hours, the reaction mixture was diluted with DCM (10 ml) and washed with HCl 0.5M. The organic layer was dried over Na2SO4 and evaporated. The crude material was purified by flash chromatography on silica gel (EtOAc 100%) affording the desired product as a white solid (200 mg, 0.334 mmol, 70.1% yield, [α]D=−27.6, c=0.45, DCM).

Provenance & Evidence