1-Phenethylamine → 3-(1-Phenylethyl)-5-(quinolin-5-YL)-1H-imidazo[4,5-B]pyridin-2(3H)-one

Participants

Reaction Conditions

Reaction Steps

6-Chloro-3-nitro-N-(1-phenylethyl)pyridin-2-amine. To a solution of 2,6-dichloro-3-nitropyridine (2.0 g, 10.4 mmol) in tetrahydrofuran (18 mL) at −78° C. was added diisopropylethylamine (2.17 mL, 12.4 mmol) and 1-phenylethanamine (1.51 g, 12.4 mmol). The reaction was maintained at −78° C. for 2 h and then allowed to slowly warm to room temperature overnight. Solvent was removed under reduced pressure and the crude product was purified by silica gel chromatography to afford the title compound (2.24 g, 78% yield). 1H NMR (400 MHz, DMSO-d6) δ 8.68 (d, J=7.5, 1H), 8.42 (d, J=8.5, 1H), 7.45 (d, J=7.5, 2H), 7.34 (t, J=7.5, 2H), 7.25 (t, J=7.5, 1H), 6.80 (d, J=8.5, 1H), 5.36 (app quint, J=7, 1H), 1.57 (d, J=7, 3H).

Provenance & Evidence