Ammonium Chloride → HCID 22663418, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3-bromo-2-(3-chlorophenoxy)pyridine (0.43 g, Reference Example 16) in dry tetrahydrofuran (6 ml), at −70° C., was treated with butyl lithium in hexane (0.64 ml, 2.5M). The mixture was then stirred at −70° C. for 45 minutes then treated with a solution of 1-benzotriazolyl 7-methoxy-2-methoxymethyl-3H-benzimidazole-4-carboxylate [0.177 g, Reference Example 1(a)] in dry tetrahydrofuran (2 ml) and stirring was continued at −70° C. for 10 minutes. The reaction mixture was allowed to warm to room temperature, then stirred at this temperature for 2 hours, then treated with aqueous ammonium chloride solution, and then extracted with ethyl acetate (20 ml). The organic extract was dried and concentrated to give a brown syrup which was purified by flash chromatography on silica eluting initially with a mixture of diethyl ether and pentane (1:1, v/v), then with a mixture of diethyl ether and pentane (7:3, v/v) and then with diethyl ether to give the title compound (0.04 g) as white solid, m.p. 181-183° C. [Elemental analysis:—C,62.17, H,4.32, N,10.15%. Calculated:—C,62.35, H,4.28, N,9.91%]. NMR (CDCl3):—δ 3.52(s,3H), 4.13(s,3H), 4.85(s,2H), 6.73(d,J=8 Hz,1H), 7.00(m,1H), 7.12(t,J=2 Hz,1H), 7.16(m,1H), 7.2(dd,J=7 Hz,J=5 Hz,1H), 7.28(t,J=8 Hz,1H), 7.55(d,J=8 Hz,1H), 7.85(dd,J=8 Hz,J=2 Hz,1H), 8.83(dd,J=4 Hz,J=1 Hz,1H).

Provenance & Evidence