Carbon Dioxide → HCID 14391164, compound

Participants

Reaction Steps

Phosgene was passed slowly into 50 ml THF until 4.46 g (0.045 mole) had been collected. To this solution was added 3.04 ml (0.844 mole) of pyrrole and the mixture stirred at 5° for 3 hours. The excess phosgene was driven off by heating and trapped in a NaOH trap to monitor CO2 evolution. The reaction mixture was cooled, treated with 10 ml pyridine followed by a solution of 2.0 g (0.012 mole) of 5-aminoindole-3-acetonitrile, Example 1, in 50 ml THF and stirred 18 hours. Methanol was added to effect complete solution and 100 g silica gel added to adsorb desired product. The solvent was removed in vacuo and treated silica gel washed with 1.5 l of EtOAc which was then concentrated in vacuo to give crude product. This was further purified by column chromatography (EtOAc/Hexane (4:1) on silica gel) to give 1.16 g (37%) desired product: m.p. 216°-218°.

Provenance & Evidence