methyl 7-(benzyloxy)-2-(3-(trifluoromethyl)phenyl)-5H-pyrido[3,2-b]indole-4-carboxylate → HCID 178497265, compound

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Reaction Steps

A solution of methyl 7-(benzyloxy)-2-(3-(trifluoromethyl)phenyl)-5H-pyrido[3,2-b]indole-4-carboxylate (1.0 g, 2.1 mmol) in TFA (8.3 mL) and water (2.3 mL) was heated at 90° C. for 3 hrs. The solvent was removed to leave an orange solid. This was suspended in DCM:hexane=1:1 and then collected by filtration to give crude methyl 7-hydroxy-2-(3-(trifluoromethyl)phenyl)-5H-pyrido [3,2-b]indole-4-carboxylate (0.9 g) as a yellow solid that was used as such. MS (ESI) m/z 387.09 (M+H). 1H NMR (500 MHz, DMSO-d6) δ ppm 11.49 (1H, s), 8.53 (1H, s), 8.49 (1H, d, J=7.02 Hz), 8.30 (1H, s), 8.11 (1H, d, J=8.24 Hz), 7.75-7.80 (2H, m), 7.13 (1H, d, J=1.83 Hz), 6.81 (1H, dd, J=8.39, 1.98 Hz), 4.07 (3H, s).

Provenance & Evidence