Trifluoroacetic acid → 4-(piperazin-1-yl)-9-((2-(trimethylsilyl)ethoxy)methyl)-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile

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Reaction Steps

A solution of tert-butyl 4-(6-cyano-9-((2-(trimethylsilyl)ethoxy)methyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrol-4-yl)piperazine-1-carboxylate (440 mg, 0.8 mmol) in methylene chloride (3 mL) was treated with trifluoroacetic acid (0.6 mL, 8.0 mmol) and the reaction mixture was stirred at ambient temperature for 4 hours. The reaction mixture was diluted with methylene chloride (50 mL) and washed with saturated aqueous sodium carbonate solution (10 mL). The organic layer was separated, dried over sodium sulfate, filtered, concentrated in vacuo, and purified flash chromatography (silica, 4 g, ISCO, 0-10% methylene chloride in methanol) to afford the title compound as a white foam, which was used in the next step without any further purification (200 mg, 60%).

Provenance & Evidence