Sodium Methoxide → 5-chloro-7-(methyloxy)-3-(1-naphthalenylmethyl)-3H-imidazo[4,5-b]pyridine

Participants

Reaction Steps

5,7-Dichloro-3-(1-naphthalenylmethyl)-3H-imidazo[4,5-b]pyridine (150 mg, 0.457 mmol) and sodium methoxide (0.157 mL, 0.686 mmol) in Methanol (1.5 mL) were irradiated in a microwave oven for 1 h at 110° C. The mixture was diluted with water, the precipitate was collected, washed with water, dried to give 5-chloro-7-(methyloxy)-3-(1-naphthalenylmethyl)-3H-imidazo[4,5-b]pyridine (143 mg, 0.318 mmol, 69.6% yield) which was used as is in the next step. MS (ES+) m/e 324 (MH+); 1H NMR (400 MHz, DMSO-d6) δ ppm 8.36 (s, 1H), 8.24 (d, J=7.83 Hz, 1H), 7.95-8.03 (m, 1H), 7.91 (d, J=8.08 Hz, 1H), 7.60 (qd, J=7.20, 5.43 Hz, 2H), 7.44 (dd, J=8.21, 7.20 Hz, 1H), 7.02 (d, J=7.07 Hz, 1H), 6.99 (s, 1H), 5.93 (s, 2H), 4.10 (s, 3H).

Provenance & Evidence