HCID 66599464, compound → HCID 66605740, compound

Participants

Reaction Steps

A solution of methyl 5-benzyl-7-methoxy-2-(piperidin-1-yl)-5H-pyrido[3,2-b]indole-4-carboxylate (51 mg, 0.12 mmol) in TFA (2 mL) and two drops of trifluoromethanesulfonic acid was heated at reflux for 30 min. Another two drops of trifluoromethanesulfonic acid was added and heating continued for another 40 min. Preparative HPLC (100×30 mm Luna C18 column, Solvent A=10 mM NH4OAc in 95% water:5% acetonitrile; B=10 mM NH4OAc in 5% water:95% acetonitrile; gradient of 15 to 100% B over 20 min at 42 mL/min) followed by removal of the solvents afforded methyl 7-methoxy-2-(piperidin-1-yl)-5H-pyrido[3,2-b]indole-4-carboxylate (15 mg, 0.044 mmol, 37% yield). MS (ESI) m/z 340.2 (M+H). 1H NMR (500 MHz, chloroform-d) δ ppm 9.02 (1H, br. s.), 8.09 (1H, d, J=8.85 Hz), 7.22 (1H, s), 6.89 (1H, s), 6.85 (1H, d, J=8.55 Hz), 4.02 (3H, s), 3.90 (3H, s), 3.53-3.64 (4H, m), 1.69-1.80 (4H, m), 1.56-1.67 (2H, m).

Provenance & Evidence