Trifluoroacetic acid → HCID 67313244, compound

Participants

Reaction Steps

To a suspension of 6-(benzyloxy)-N2-(4-bromophenyl)pyridine-2,3-diamine (3.86 g, 10.4 mmol) in H2O was added cyanogen bromide (1.44 g, 13.5 mmol) and TFA (200 μL). The reaction mixture was stirred at room temperature for 2.5 h, added 2 M aqueous Na2CO3 and extracted with DCM. The organic extract was dried over MgSO4, filtered, and concentrated. The residue was purified by column chromatography to give 5-(benzyloxy)-3-(4-bromophenyl)-3H-imidazo[4,5-b]pyridin-2-amine intermediate. The benzyl group was removed in a similar manner as the one described in Example 1.102 to give the title compound. LCMS m/z=305.1 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 6.22 (broad s, 2H), 6.29 (d, J=8.2 Hz, 1H), 7.39-7.46 (m, 3H), 7.77 (m, 2H), 9.96 (s, 1H).

Provenance & Evidence