Acetic Acid → HCID 86663055, compound

Participants

Reaction Steps

Sodium cyanoborohydride (0.655 mL, 0.655 mmol, 1.0 M in THF) was added to a mixture of 7-amino-2-bromo-5H-pyrido[3,2-b]indole-4-carboxamide (100 mg, 0.262 mmol), formaldehyde (0.21 mL, 2.6 mmol, 37% aq. solution), and acetic acid (0.45 mL, 0.79 mmol), in a mixture of MeOH (1 mL) and THF (1 mL). After stirring for 1 hr, this was diluted with MeOH and preparative HPLC (PHENOMENEX® Luna C18 30×100 10u Column, Solvent A=10 mM NH4OAc in 95% water:5% acetonitrile; B=10 mM NH4OAc in 5% water:95% acetonitrile, 30 to 100% B over 20 min at 30 mL/min) followed by SCX capture and release with 2 N solution NH3 in MeOH afforded 2-bromo-7-(dimethylamino)-5H-pyrido[3,2-b]indole-4-carboxamide (70 mg, 0.17 mmol, 66% yield) as a yellow solid. MS (ESI) m/z 333.02 (M+H). 1H NMR (500 MHz, DMSO-d6) δ ppm 11.24 (1H, s), 8.37 (1H, br. s.), 7.91 (1H, d, J=8.85 Hz), 7.82 (2H, s), 6.95 (1H, s), 6.80 (1H, dd, J=8.85, 2.14 Hz), 3.04 (6H, s).

Provenance & Evidence