2-oxo-2,3-Dihydrobenzooxazole-5-boronic acid → 5-(2-Chloro-10,11-dihydro-dibenzo[a,d]cyclohepten-5-ylidenemethyl)-3H-benzooxazol-2-one

Participants

Reaction Steps

Following procedures essentially as described in Example 219 and using 5-bromomethylene-2-chloro-10,11-dihydro-5H-dibenzo[a,d]cycloheptene (200 mg, 0.630 mmol) and 2-oxo-2,3-dihydro-benzooxazole-5-boronic acid (134 mg, 0.750 mmol), provides the title compound. Purify by UV-guided semi-prep reverse-phase HPLC to obtain 14 mg (6%) of the Z-isomer (Example 222(a)) of title compound as a white solid (MS (ES) 391 (M+NH4), 372 (M−H); HPLC shows 94% purity) and 5 mg (2%) of the E-isomer (Example 222(b)) of the title compound as a white solid. MS (ES) 391 (M+NH4), 372 (M−H); HPLC shows 96% purity.

Provenance & Evidence