Bromoethene → n-[3-(2-Methyl-9,10-dihydro-1-oxa-3-aza-benzo[f]azulen-4-ylidenemethyl)-phenyl]-methanesulfonamide

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Reaction Steps

Prepare the corresponding ketone (2-methyl-9,10-dihydro-1-oxa-3-aza-benzo[f]azulen-4-one) as described by E. E. Galantay, et al, J. Med. Chem. (17) 1316-1327 (1974) and convert to the corresponding Z-isomer of the vinyl bromide using procedures essentially as described in Preparations 23 and 24. Then, following procedures essentially as described in Example 219, combine the ketone with 3-methanesulfonamidophenyl boronic acid (325 mg, 1.5 mmmol). Purify the crude product using column chromatography (30% EtOAc/hexane to 50% EtOAc/hexane) to provide 180 mg (38%) Z-isomer as a light tan solid, mp 184.6° C., MS (ES) 381 (M+1), 379 (M−1). HPLC shows 94% purity at t=1.99 min.

Provenance & Evidence