HCID 178418546, compound → HCID 178437440, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-bromo-2-ethyl-7-methyl-3-(2'-(tetrazol-5-yl)biphen-4-yl)methyl-3H-imidazo[4,5-b]pyridine (41 mg), CuCN (80 mg), and pyridine (0.2 mL) was heated with stirring to 160° C. for 4 hours. The pyridine distilled off during the course of the heating. The cooled dark mass was dissolved in 2 mL of 20% aqueous KCN by heating to 50° C. for 15 minutes. Acetic acid (2 mL) (Caution! HCN is evolved.) was added and the mixture was extracted (2×EtOAc). The organic layers were dried (Na2SO4), concentrated, and purified (SiO2, 80/20/1 CH2Cl2 --MeOH--NH4OH) to give 26 mg of the title compound as a solid. 1H NMR (250 MHz, CD3OD) δ7.66-7.45 (m, containing a singlet at 7.57, 5H), 7.15-7.04 (m, 4H), 5.53 (s, 2H), 2.91 (q, 2H, J=7.5 Hz), 2.66 (s, 3H), 1.27 (t, 3H, J=7.5 Hz).

Provenance & Evidence