Synthesis
GENERAL METHOD: 2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetic acid (1 eq.) and BOP-Cl (1 eq.) were suspended in dichloromethane (20 mL/g of acid), triethylamine (2 eq.) was added slowly and the mixture was stirred for 10 minutes. Methanol (4 eq.) was then added and the reaction mixture continued to be stirred for at least 12 hours. Upon completion of the reaction, the solvent was removed by evaporation and the resulting solid was purified by column chromatography with the eluent being a solvent mixture of hexane and ethyl acetate (3:1, v/v) at a boiling range of 80-100°C. Finally, the solvent was removed under reduced pressure to give methyl 2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetate as a light yellow solid.
References
[1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 15, p. 4830 - 4837
[2] Pharmazie, 2003, vol. 58, # 2, p. 99 - 103
[3] Patent: CN105418480, 2016, A. Location in patent: Paragraph 0031
[4] Bioorganic and Medicinal Chemistry, 2001, vol. 9, # 3, p. 745 - 762
[5] European Journal of Pharmaceutical Sciences, 2001, vol. 14, # 4, p. 301 - 311
