Acetic Acid → tert-butyl(1-(4-(5-oxo-3-phenyl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-2-yl)phenyl)cyclobutyl)carbamate

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl(1-(4-(3-(dimethylamino)-2-phenylacryloyl)phenyl)cyclobutyl)carbamate (119 mg, 0.28 mmol) in acetic acid (1 mL) was added molecular sieves (10 mg) and cycloheptane-1,3-dione (36 μL, 0.42 mmol) under nitrogen. The resulting mixture was heated at 100° C. for 2 h. After cooled down to room temperature, the mixture was partitioned between water (10 mL) and dichloromethane (10 mL). The layers were separated and the aqueous phase extracted into dichloromethane (2×10 mL). The combined organic phases were washed with saturated NaHCO3 solution (20 mL), brine (20 mL), dried over Na2SO4, filtered and concentrated to dryness under reduced pressure. The resulting residue was purified by Biotage silica gel chromatography (gradient 0 to 20% EtOAc in hexane) to give the title compound (32 mg, 24%). 1H NMR (500 MHz, CDCl3): 8.09 (1H, s), 7.38 (2H, d), 7.30 (2H,d), 7.25-7.24 (3H, m), 7.19-7.17 (2H, m), 5.04 (1H, br s), 3.29 (2H,t), 2.87 (2H, t), 2.60-2.25 (4H, m), 2.07-2.01 (3H, m), 1.99-1.94 (2H, m), 1.84-1.75 (1H, m), 1.42-1.15 (9H, br).

Provenance & Evidence