2-Bromobenzaldehyde → tert-butyl 1-(4-(1-oxo-3-phenyl-1H-inden-2-yl)phenyl)cyclobutylcarbamate

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-bromobenzaldehyde (92.5 mg, 0.5 mmol), tert-butyl 1-(4-(phenylethynyl)phenyl)cyclobutylcarbamate (347 mg, 1.0 mmol), sodium acetate (164 mg, 2.0 mmol), tetrabutylammonium chloride hydrate (147.7 mg, 0.50 mmol) and palladium acetate (5.6 mg, 0.025 mmol) in DMF (10 mL) was heated at 100° C. for 48 h. The reaction mixture was concentrated to dryness and was partitioned between ethyl acetate (30 mL) and water (30 mL). The organic phase was washed with water (30 mL), brine (20 mL), dried (Na2SO4), filtered and concentrated in vacuo. The crude residue was purified by column chromatography (eluting with 10% ethyl acetate in hexane) to give title compound (14 mg, 6.2%). 1H NMR (500 MHz, CDCl3): 7.50 (d, 1H), 7.45-7.05 (m, 12H), 2.55-2.25 (m, 4H), 2.15-1.95 (m, 1H), 1.85-1.70 (m, 1H), 1.40-1.10 (br s, 9H).

Provenance & Evidence