Potassium Carbonate → {5-methoxy-1-methoxycarbonylmethyl-3-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-1H-indol-6-yloxy}acetic acid

Participants

Reaction Steps

A solution of 5-methoxy-3-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-1H-indol-6-ol (0.043 g; 100 μmol), in solution in dimethylformamide (10 ml), is placed in a 1.3×10 cm hemolysis tube, then potassium carbonate (0.027 g; 200 μmol) is added and the mixture is agitated at ambient temperature for 5 minutes. Methyl bromoacetate (0.028 ml; 300 μmol) is added and the mixture is then heated at 50° C. for 4 hours, the TLC control (eluent: 50/50 v/v cyclohexane/ethyl acetate) showing that the reaction has come to an end. The reaction mixture is run into 5 ml of distilled water and the reaction mixture is then extracted with ethyl acetate (15 ml). The combined extracts are washed with water (20 ml), dried over magnesium sulfate, filtered, and evaporated to give a crude compound which is purified by chromatography on silica gel, elution being carried out with a mixture of cyclohexane and ethyl acetate (60/40 v/v). The fractions containing the expected compound are combined and evaporated to give the methyl ester of {5-methoxy-1-methoxycarbonylmethyl-3-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-1H-indol-6-yloxy}acetic acid (0.056 g; 97%), the characteristics of which are as follows:

Provenance & Evidence