Methyl 3-azido-2,6-bis(4-methoxyphenyl)isonicotinate → methyl 7-methoxy-2-(4-methoxyphenyl)-5H-pyrido[3,2-b]indole-4-carboxylate

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Reaction Steps

A solution of methyl 3-azido-2,6-bis(4-methoxyphenyl)isonicotinate (230 mg, 0.589 mmol) in 1,2-dichlorobenzene (5 mL) was heated at 170° C. with gas evolution. After 0.5 hr, the solvent was removed under vacuum and silica gel radial chromatography of the residue (step gradient elution with hexane containing 5 to 20% ethyl acetate) afforded methyl 7-methoxy-2-(4-methoxyphenyl)-5H-pyrido[3,2-b]indole-4-carboxylate (153 mg, 72%) as a yellow solid. MS (ESI) m/z 363.1 (M+H). 1H NMR (CDCl3) δ ppm 9.39 (1H, s), 8.29 (1H, d, J=8.55 Hz), 8.13 (1H, s), 8.10 (2H, d, J=8.85 Hz), 7.03 (2H, d, J=8.85 Hz), 6.93-6.99 (2H, m), 4.07 (3H, s), 3.93 (3H, s), 3.88 (3H, s).

Provenance & Evidence