Iodine → HCID 178521006, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (R)-3-(5-(3-(pyrrolidine-1-carbonyl)piperidin-1-yl)-3H-imidazo[4,5-b]pyridin-2-yl)benzonitrile (30 mg, 0.07 mmol) in N,N-dimethylformamide (2 mL) were added sodium azide (6 mg, 0.09 mmol) and iodine (3 mg). The reaction mixture was heated for 12 h at 120° C., then was cooled. The mixture was filtered, and the filtrate was concentrated. The resulting residue was triturated with diethyl ether to afford (R)-(1-(2-(3-(2H-tetrazol-5-yl)phenyl)-3H-imidazo[4,5-b]pyridin-5-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone as yellow solid (36 mg, 92%). MS (ES+APCI) (M+H) 444.1; HPLC retention time 3.551 min (Method C1). 1H NMR (400 MHz, DMSO-d6) δ 1.50-2.00 (m, 8H), 2.60-2.68 (m, 1H), 2.83-2.97 (m, 3H), 3.25-3.31 (m, 1H), 3.42-3.50 (m, 1H), 3.52-3.60 (m, 1H), 4.32 (d, 1H), 4.42 (d, 1H), 6.83 (d, 1H), 7.47 (t, 1H), 7.81 (d, 1H), 7.94-8.02 (m, 2H), 8.79 (s, 1H), 13.02 (s, 1H).

Provenance & Evidence