Z-6-chloro-3-(3-chloro-benzylidene)-2-oxo-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester → 2'-[5-bromo-2-(tetrahydro-pyran-4-yloxy)-phenyl]-6-chloro-4'-(3-chlorophenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

Participants

Reaction Steps

In a manner similar to the method described in example 32d, E/Z-6-chloro-3-(3-chloro-benzylidene)-2-oxo-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester prepared in example 5b (1.0 g, 2.5 mmol) was reacted with 1-[5-bromo-2-(tetrahydro-pyran-4-yloxy)-phenyl]-3-trimethylsilyoxy-2-aza-1,3-butadiene (4 g, 10 mmol) in toluene at 140° C., then treated with trifuloroacetic acid in dicloromethane to give racemic(2′R, 3R, 4′S)-2′-[5-bromo-2-(tetrahydro-pyran-4-yloxy)-phenyl]-6-chloro-4′-(3-chlorophenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as a yellow solid (Yield 0.76 g, 49%)

Provenance & Evidence