2-(Dimethylamino)ethanol → HCID 66604403, compound

Participants

Reaction Steps

Diethyl azodicarboxylate (0.057 mL, 0.360 mmol) was added to an ice-cooled solution of triphenylphosphine (94 mg, 0.360 mmol) in dry THF (1 mL). The bath was removed and a solution of 7-hydroxy-2-(4-methoxyphenyl)-5H-pyrido[3,2-b]indole-4-carboxamide (Example 207, 60 mg, 0.180 mmol) and 2-(dimethylamino)ethanol (24 mg, 0.270 mmol) in dry THF (1 mL) was added after 15 minutes. After stirring for 2 hr at room temperature, the reaction was quenched with brine and extracted with EtOAc. The extracts were dried with sodium sulfate and the solvent was removed. Radial silica gel chromatography of the residue (step gradient elution with methylene chloride containing 10 to 60% methanol) followed by SCX cartridge purification gave 7-(2-(dimethylamino)ethoxy)-2-(4-methoxyphenyl)-5H-pyrido[3,2-b]indole-4-carboxamide (12 mg) as a yellow glass. MS (ESI) m/z 405.1 (M+H). 1H NMR (DMSO-d6) δ ppm 11.34 (1H, br. s.), 8.56 (1H, s), 8.28 (1H, s), 8.23 (2H, d, J=8.85 Hz), 8.10 (1H, d, J=8.55 Hz), 7.83 (1H, s), 7.28 (1H, d, J=2.14 Hz), 7.10 (2H, d, J=8.85 Hz), 6.89 (1H, dd, J=8.55, 2.44 Hz), 4.15 (2H, t, J=5.95 Hz), 3.85 (3H, s), 2.70 (2H, t, J=5.80 Hz), 2.27 (6H, s).

Provenance & Evidence