3-(Ethylsulfonamido)phenylboronic acid → Ethanesulfonic acid [3-(1-chloro-10,11-dihydro-dibenzo[a,d]cyclohepten-5-ylidenemethyl)-phenyl]-amide

Participants

Reaction Steps

Following procedures essentially as described in Example 219, below, and using 5-bromomethylene-1-chloro-10,11-dihydro-5H-dibenzo[a,d]cycloheptene (100 mg, 0.313 mmol) and 3-ethanesulfonylaminophenylboronic acid (79 mg, 0.344 mmol), affords 112 mg (84%) of a mixture of geometric isomers of the title compound (Example 208(a)) as a yellow solid (MS (ES) 424 (M+H); HPLC shows 94% purity). Separate geometric isomers using a chromatatron rotor (10% ethyl acetate/hexanes) to afford 13 mg (10%) of the Z-isomer (Example 208(b)) of the title compound as a white solid, (MS (ES) 424 (M+H), 422 (M−H). HPLC shows 96% purity). Continue to elute and isolate 6 mg (5%) of the E-isomer (Example 208(c))of the title compound as a white solid (MS (ES) 424 (M+H), 422 (M−H); HPLC shows 97% purity).

Provenance & Evidence