Pyridine → HCID 53834776, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 0.63 g (1.34 mmol) of N-methyl-N-phenethyl-2-(5-benzyloxy-3-(2-carboxyvinyl)indol-1-yl]-acetamide in 15 ml of methylene chloride, cooled to 0° C. with an external ice bath, is added dropwise 0.26 ml (3.02 mmol) of oxalyl chloride, followed immediately with 3 drops of N,N-dimethylformamide. The mixture is stirred in an ice bath for 30 minutes and then for 1 hour with the cooling bath removed. The reaction mixture is then concentrated in vacuo. The residue obtained is dissolved in 10 ml of methylene chloride and this solution is added dropwise to a mixture of 0.11 ml (1.34 mmol) of pyrrolidine, 0.24 ml of pyridine and 15 ml of methylene chloride with stirring at 0° C. (ice bath). The resulting reaction mixture is stirred at room temperature for several hours and quenched with saturated aqueous NH4Cl solution. Ethyl acetate and water are added and the layers separated. The organic layer is washed with 1N aqueous HCl solution and water, dried over magnesium sulfate and concentrated in vacuo. The residue is triturated in hot ethyl acetate to give N-methyl-N-phenethyl-2-[5-benzyloxy-3-(2-(1-pyrrolidinecarbonyl)-vinyl)indol-1-yl]acetamide (m.p. 185°-187° C.).

Provenance & Evidence