Methyl vinyl ketone → HCID 86722449, compound

Participants

Reaction Steps

TEA (0.300 mL, 2.152 mmol) was added to a slurry of 10-bromo-1-(4-fluorophenyl)-6-hydroxy-7,8-dihydro-1H-oxepino[3,2-f]indazole-5-carbonitrile (102, R1=4-Fluorophenyl) (3.15 g, 7.87 mmol) in DME (40.0 mL) under a nitrogen atmosphere. Methyl vinyl ketone (1.30 mL, 15.8 mmol) was added dropwise. After about 47 h, the volatiles were removed under reduced pressure to afford 10-bromo-1-(4-fluorophenyl)-6-oxo-5-(3-oxobutyl)-5,6,7,8-tetrahydro-1H-oxepino[3,2-f]indazole-5-carbonitrile as a tan foam. LC/MS, method 3, Rt=2.33 min, MS m/z 470 and 472 (M+H)+. The material was dissolved in toluene (80 mL) in a 250 mL round bottom with Dean-Stark trap and reflux condenser attached under a nitrogen atmosphere. Toluene-4-sulfonic acid hydrate (0.599 g, 3.15 mmol) was added. After about 3 h at reflux, the mixture was allowed to cool to rt. Sat. aq. NaHCO3 (100 mL) was added.

Provenance & Evidence