Toluene → HCID 86722452, compound

Participants

Reaction Steps

A solution of 8-bromo-9-(4-fluorophenyl)-3-oxo-2,3,5,6,9,12b-hexahydro-1H-benzo[4,5]oxepino[3,2-f]indazole-12b-carbonitrile (103, R1=4-Fluorophenyl) (2.02 g, 4.47 mmol) and toluene (80 mL) was added to 20% palladium hydroxide on carbon (wet, Deguessa type, 0.314 g). The mixture was shaken under about 50 psi of hydrogen at about 55° C. After about 17 h, the reaction mixture was allowed to cool to rt then filtered through Celite® rinsing with 25% THF/toluene (4×50 mL) then 25% THF/DCM (6×25 mL). The volatiles were removed under reduced pressure to afford a light tan solid which was slurried in DCM (10 mL). The solid was collected by filtration rinsing with DCM (3×10 mL) then dried under reduced pressure to afford (4aR,12bS)-8-bromo-9-(4-fluorophenyl)-3-oxo-2,3,4,4a,5,6,9,12b-octahydro-1H-benzo[4,5]oxepino[3,2-f]indazole-12b-carbonitrile; compound with (4aS,12bR)-8-bromo-9-(4-fluorophenyl)-3-oxo-2,3,4,4a,5,6,9,12b-octahydro-1H-benzo[4,5]oxepino[3,2-f]indazole-12b-carbonitrile (104, R1=4-Fluorophenyl) (0.916 g, 45% yield) as an ivory solid. The mother liquor was concentrated under reduced pressure.

Provenance & Evidence