反应详情

A mixture of 3-ethoxy-5-methoxy-1-phenyl-1H-indole-2-carboxylic acid (0.11 g, 0.35 mmol; Unangst PC, et al., J. Med. Chem. 1989;32:1360) and 1,1'-carbonyldiimidazole (0.065 g, 0.40 mmol) in 5.0 mL of tetrahydrofuran is stirred at reflux for 90 minutes. The mixture is cooled slightly and 5.0 mL of concentrated ammonium hydroxide is added. After stirring for an additional 90 minutes, the mixture is partitioned between ethyl acetate and brine. The organic layer is washed several times with fresh brine, dried (anhydrous sodium sulfate) and evaporated. Recrystallization of the residue from ethyl acetate-hexane yields 0.082 g (75%) of product; mp 143°-144° C.

1. temperatureat reflux for 90 minutes
2. temperatureThe mixture is cooled slightly
3. stirringAfter stirring for an additional 90 minutes
4. customthe mixture is partitioned between ethyl acetate and brine
5. washThe organic layer is washed several times with fresh brine
6. dry with materialdried (anhydrous sodium sulfate)
7. customevaporated
8. customRecrystallization of the residue from ethyl acetate-hexane