1-(5-Fluoro-2-methylphenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene → Racemic (2'S,3S,4'R)-6-chloro-4'-[5-chloro-2-(3-methyl-oxetan-3-ylmethoxy)-phenyl]-2'-(5-fluoro-2-methyl-phenyl)-spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(5-fluoro-2-methyl-phenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene (7.1 mmol) in anhydrous toluene (7 mL) was added E/Z-6-Chloro-3-[5-chloro-2-(3-methyl-oxetan-3-ylmethoxy)-benzylidene]-2-oxo-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester (0.7 g, 1.4 mmol). The solution was stirred under Ar in a sealed tube at 140° C. for 3 h. After the solution was cooled to room temperature and concentrated, the residue was purified by chromatography (DCM:CH3OH=50:1) to give crude product. The crude product was purified again by Prep-HPLC to give title compound as a white solid (12 mg).

Provenance & Evidence