Sodium Iodide → 3-(2-Fluoro-4-iodo-phenylamino)-1-(2-methoxy-ethyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl ester

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Reaction Conditions

Reaction Steps

A mixture of 3-(2-Fluoro-4-iodo-phenylamino)-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl ester (234 mg, 0.55 mmol), potassium carbonate (91 mg, 0.66 mg), sodium iodide (103 mg, 0.69 mmol) and 1-bromo-2-methoxy-ethane (0.057 mL, 0.61 mmol) in DMF (5 mL) was stirred a 90° C. for 2 days. It was cooled to room temperature, diluted with water and extracted into ethyl acetate. The organic layer was separated then washed with water followed by brine, then dried (Na2SO4), filtered and concentrated to give a residue which was purified by flash chromatography (Si-PPC, ether:pentane, gradient 20:80 to 50:50) to provide the title compound as a yellow oil (44 mg, 16%). LCMS (method B): RT=2.56 min, M+H+=483.

Provenance & Evidence