反应详情

温度

100 °C

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).

1. concentrationThe reaction mixture was concentrated to dryness
2. customwas partitioned between ethyl acetate (30 mL) and water (30 mL)
3. washThe organic phase was washed with water (30 mL), brine (20 mL)
4. dry with materialdried (Na2SO4)
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe crude residue was purified by column chromatography (eluting with 10% ethyl acetate in hexane)