Diethyl Ether → 7-(2-methoxyethoxy)-2-(4-methoxyphenyl)-5H-pyrido[3,2-b]indole-4-carboxamide

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Reaction Steps

Methyl 3-amino-2-(4-(benzyloxy)phenyl)-6-(4-methoxyphenyl)isonicotinate (556 mg, 1.262 mmol) was dissolved in trifluoroacetic acid (6 mL) and the yellow solution cooled in an ice bath. Solid sodium nitrite (174 mg, 2.52 mmol) was added with stirring to give a dark red mixture. After 30 min, solid sodium azide (821 mg, 12.6 mmol) was added followed by diethyl ether (6 mL). The light red mixture was stirred in the ice bath for 30 min. The reaction was concentrated on the rotary evaporator and was then partitioned between EtOAc and sufficient saturated aqueous NaHCO3 solution (gas evolution) to neutralize the acid. The organic phase was separated, washed with brine, dried with sodium sulfate, and the solvent removed. Radial silica gel chromatography (step gradient elution with hexane containing 0 to 20% EtOAc) afforded the two major products as oils:

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