Dimethylformamide → 1-cyclohexylmethyl-3-(3,4-dimethyl-benzoyl)-1H-quinolin-4-one

Participants

Reaction Steps

The titled compound was prepared following the procedure described in Step 3 of Example 1. 63 mg (0.23 mmol) of 3-(3,4-dimethyl-benzoyl)-1H-quinolin-4-one 3a, 12 mg (0.30 mmol) of 60% sodium hydride and 52 mg (0.30 mmol) of cyclohexylmethyl bromide and 0.9 mL N,N-dimethylformamide were combined at 90° C. for 5 h. Flash chromatography using 10-75% ethyl acetate in hexane yielded 50 mg of the product 4b as white solid: LC-MSD, m/z for C25H27NO2 [M+H]+=374.6; HPLC retention time: 2.8 min; 1H NMR (400 MHz, CDCl3): δ 1.0-1.3 (m, 6H), 1.7-1.85 (m, 4H), 1.9-2.0 (m, 1H), 2.3 (s, 3H), 2.35 (s, 3H), 4.0-4.05 (m, 2H), 7.15-7.2 (m, 1H), 7.4-7.5 (m, 2H), 7.5-7.6 (m, 1H), 7.6 (s, 1H), 7.65-7.75 (m, 1H), 8.05 (s, 1H), 8.45-8.5 (m, 1H).

Provenance & Evidence