Water → methyl 3-[(9-chloro-4-methyl-5-oxo-2,3,4,5-tetrahydro-1,4-benzoxazepin-8-yl)oxy]-5-[(3S)-tetrahydrofuran-3-yloxy]benzoate

Participants

Reaction Steps

A solution of N-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-3-chloro-2,4-difluoro-N-methylbenzamide (647 mg, 1.78 mmol) in acetonitrile (10 mL) was heated with potassium carbonate (492 mg, 3.56 mmol) and methyl 3-hydroxy-5-[(3S)-tetrahydrofuran-3-yloxy]benzoate (424 mg, 1.78 mmol) at 160° C. for 2.5 hours in a microwave reactor. Water (15 mL) and ethyl acetate (20 mL) was added to the reaction mixture, the layers separated and the aqueous phase extracted with ethyl acetate (3×20 mL). The combined organic extract was washed with brine (10 mL) and dried (MgSO4), filtered and evaporated to a residue which was chromatographed on silica, eluting with 40-100% ethyl acetate in isohexane, to give the desired compound as a clear oil (200 mg).

Provenance & Evidence