Potassium Carbonate → Methyl 4-{[3-(pyridin-4-yl)propyl]sulfanyl}benzoate

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of 4-mercapto-benzoic acid methyl ester (506 mg, 3.01 mmol) and potassium carbonate (1.245 g, 9.01 mmol) in dimethylformamide (10 mL), is added methanesulfonic acid 3-pyridin-4-yl-propyl ester (See Intermediate 14) in dicholoromethane (11 mL, 2.73 mmol). The dichloromethane is removed in vacuo and then the reaction is heated to 100° C. for 4 h. The reaction is allowed to cool to room temperature and washed with water while extracting with ethyl acetate. The organic portion is concentrated in vacuo. The resulting residue is purified using radial chromatography, eluting with methanol and dichloromethane to obtain 174 mg (22%) of the title compound. MS (ES+) m/e 288.1 (M+1)+.

Provenance & Evidence