Triethylamine → HCID 22727956, compound

Participants

Reaction Steps

A solution of 5-bromo-2-chloro-3-nitropyridine (7.0 g, 29 mmol) and 3-(pyridin-3-yl)phenylamine (5.0 g, 29 mmol) in 1-methyl-2-pyrrolidinone (10 ml) and triethylamine (4 ml, 29 mmol) was heated at 100° C. for 90 minutes. The reaction was cooled, suspended in ethyl acetate (400 ml) and insoluble material removed by filtration. The filtrate was then washed with water, brine and dried over anhydrous sodium sulphate. This solution was filtered and pre-adsorbed on to silica gel. Purification by silica gel chromatography eluting with hexane containing triethyline (1%) on a gradient of ethyl acetate from 20% to 35% gave N-(5-bromo-3-nitropyridin-2-yl)-N-[3-(pyridin-3-yl)phenyl]amine as a red solid (5.1 g, 47%); δH (400 MHz, CDCl3) 7.35-7.45 (2H, m, ArH), 7.51 (1H, t, J 8, ArH), 7.62 (1H, d, J 8, ArH), 7.88-7.91 (2H, m, pyridyl-H and NH), 8.53 (1H, s, pyridyl-H), 8.62 (1H, d, J 5, pyridyl-H), 8.68 (1H, s, pyridyl-H), 9.88 (1H, s, pyridyl-H), 10.14 (1H, s, pyridyl-H); m/z (ES+) 371 and 373 (M++H).

Provenance & Evidence