Triethylamine → HCID 59740593, compound

Participants

Reaction Conditions

Reaction Steps

A 25-mL round bottomed flask was cooled to 0° C. with an ice/water bath and charged with 5-(3-amino-2-methylphenyl)-3-bromo-1-methylpyridin-2-one (12) (0.71 g, 2.20 mmol), triethylamine (489 mg, 4.84 mmol), methylene chloride (10 mL) and 4-tert-butyl-benzoyl chloride (0.48 g, 2.42 mmol) and the reaction mixture stirred at room temperature for 18 h. After this time the reaction was partitioned between water (25 mL) and ethyl acetate (50 mL). The organic layer was separated and washed with saturated aqueous sodium bicarbonate (2×25 mL), brine (50 mL) and dried over magnesium sulfate. The drying agent was removed by filtration and the filtrate concentrated under reduced pressure. The resulting residue was subjected to flash chromatography to afford 0.75 g (75%) of N-(3-(5-bromo-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-2-methylphenyl)-4-tert-butylbenzamide (13) as a white solid: mp 149-151° C.; 1H NMR (300 MHz, CDCl3) 7.87 (dd, 1H, J=2.4 Hz), 7.86 (d, 2H, J=8.4 Hz), 7.71 (br s, 1H), 7.54 (d, 2H, J=8.7 Hz), 7.30 (t, 1H, J=7.8 Hz), 7.27 (d, 1H, J=1.8 Hz), 3.75 (br s, 2H), 7.05 (dd, 1H, J=7.8, 1.5 Hz), 3.67 (s, 3H), 2.24 (s, 3H), 1.37 (s, 9H); MS (ESI+) m/z 453 (M+H).

Provenance & Evidence