N,N-Dimethylformamide--water (1/1) → HCID 68458101, compound

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Reaction Steps

3-[4-(Benzyloxy)phenyl]-6-bromo-3H-imidazo[4,5-b]pyridine (2 g, 5.26 mmol), Zn(CN)2 (371 mg, 3.16 mmol), Pd2(dba)3 (101 mg, 0.11 mmol) and dppf (122 mg, 0.22 mmol) in degassed DMF/H2O (100:1) (15 mL) was stirred at 120° C. under N2 for 20 h. The mixture was then cooled to rt and treated with NH4Cl:NH4OH:H2O (4:1:4) (45 mL) and reheated to 80° C. for 30 min and then stirred at 0° C. for another 30 min. The precipitated solids were isolated by filtration and purified by chromatography over silica gel eluting with 50% EtOAc/hexane to give 3-[4-(benzyloxy)phenyl]-3H-imidazo[4,5-b]pyridine-6-carbonitrile. 1H NMR (400 MHz, D6-Acetone) δ 5.16 (s, 2H), 7.18 (d, J=8 Hz, 2H), 7.36-7.47 (m, 5H), 7.57 (d, J=8 Hz, 2H), 8.41 (s, 1H), 8.44 (d, J=2 Hz, 1H) and 8.70 (d, J=2 Hz, 1H); MS (ES+): m/z 327 [MH+].

Provenance & Evidence