Acetic Acid → HCID 86663039, compound

Participants

Reaction Steps

A suspension of methyl 2-bromo-8-formyl-5H-pyrido[3,2-b]indole-4-carboxylate (200 mg, 0.600 mmol) in DMF (1 mL) was stirred for 5 min and then diluted with DCM (10 mL). Morpholine (0.063 mL, 0.720 mmol) was added and the suspension was cooled in an ice bath. Sodium triacetoxyborohydride (344 mg, 1.62 mmol) was added and the suspension was left stirring for 0.5 hr. Acetic acid (0.069 mL, 1.20 mmol) was then added and the bath removed. The reaction was left stirring at RT overnight. It was diluted with DCM and washed with sat. aq. NaHCO3 solution followed by water (2×). After drying with sodium sulfate, the solvent was removed and radial chromatography (step gradient elution with DCM containing 0 to 3% MeOH) afforded methyl 2-bromo-8-(morpholinomethyl)-5H-pyrido[3,2-b]indole-4-carboxylate (143 mg, 0.354 mmol, 59% yield) as dark green solid. MS (ESI) m/z 436.10 (M+H). 1H NMR (400 MHz, chloroform-d) δ ppm 9.55 (1H, br. s.), 8.27 (1H, s), 7.94 (1H, s), 7.56 (1H, dd, J=8.31, 1.51 Hz), 7.45 (1H, d, J=8.31 Hz), 4.04 (3H, s), 3.66-3.74 (4H, m), 3.64 (2H, s), 2.46 (4H, br. s.).

Provenance & Evidence