1-(3-Fluorophenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene → Racemic (2'S,3S,4'R)-4'-[5-bromo-2-(1-tert-butoxycarbonyl-piperidin-4-yloxy)-phenyl]-6-chloro-2'-(3-fluorophenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(3-fluoro-phenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene in example 36a (24 mmol) in toluene (100 mL) was added E/Z-3-[5-bromo-2-(1-tert-butoxycarbonyl-piperidin-4-yloxy)-benzylidene]-6-chloro-2-oxo-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester (3.85 g, 6 mmol). The reaction mixture was stirred under argon at 140° C. for 5 h. After cooled to room temperature, the mixture was concentrated. The residue was purified by chromatography (20%-30% EtOAc:DCM) to give the title compound as a off white solid (Yield: 0.38 g).

Provenance & Evidence