Methanol → 1-[(4-Chlorophenyl)methyl]-5-hydroxy-3-methyl-1H-indole-2-propanoic acid

Participants

Reaction Conditions

Reaction Steps

Beginning with 3-[1-p-chlorobenzyl-5-methoxy-3-methylindol-2-yl]propionic acid which is described in J. Med. Chem., 1252 (1968), (2.7 g) was dissolved in 20 ml CH2Cl2 at 0° C. 7.6 ml BBr3 (1M in CH2Cl2) was added dropwise and the reaction stirred for 60 minutes. After 180 minutes at 23° C., another 4 ml BBr3 solution was added. The reaction was stirred for a further 180 minutes. The reaction was cooled to -20° C. and 15 ml MeOH added. The organic phase was washed with NaHCO3 (aqueous), dried with Na2SO4 and chromatographed on silica gel. Hydrolysis of the methyl ester was carried out as described in Example 2 to yield 2.2 g of the title compound.

Provenance & Evidence