Sodium Methoxide → HCID 178437428, compound

Participants

Reaction Steps

A solution of sodium methoxide in methanol (30% w/v, 4 mL) was added to a solution of 2-ethyl-5,7-dimethyl-3-[(2'-(1-(4-nitrophenyl)-1H-tetrazol-5-yl)biphenyl-4-yl)methyl]-3H-imidazo[4,5-b]pyridine (A) (1.0 g) in methanol (20 mL) and the mixture was heated under reflux for 18 hours. The mixture was cooled to ambient temperature and solvent was removed by evaporation. The residue was dissolved in water (50 mL) and the solution was extracted with ether (2×50 mL). The aqueous layer was separated and adjusted to pH 5 with 1M citric acid solution. The product was collected by filtration and dried to give 2-ethyl-5,7-dimethyl-3-[(2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methyl]-3H-imidazo[4,5-b]pyridine (0.6 g) as a solid, m.p. 175°-177° C. (decomposition); NMR (d6 -acetone): 1.26(t, 3H), 2.50(s, 3H), 2.53(s, 3H), 2.76(q, 2H), 5.49(s, 2H), 6.91(s, 1H), 7.07(d, 2H), 7.14(d, 2H), 7.6(m, 3H), 7.75(dd, 1H); mass spectrum (+ve fast atom bombardment (FAB), DMSO nitrobenzyl alcohol): 410(M+H)+ ; microanalysis, found C, 64.9; H, 5.6; N, 22.0%; C24H23N7.2.0H2O requires: C, 64.7; H, 6.0; N, 22.0%.

Provenance & Evidence