Sodium Thiosulfate → 7-Chloro-3-(2-fluoro-4-iodo-phenylamino)-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl ester

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Reaction Steps

To a solution of 7-chloro-3-(2-fluoro-4-trimethylsilanyl-phenylamino)-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl ester (0.91 g, 2.25 mmol) in dichloromethane (20 ml) at −10° C. was added iodine monochloride (4.95 ml, 4.95 mmol, 1M solution in dichloromethane) and the resultant mixture was stirred at −10° C. to 0° C. for 2 h. A saturated solution of sodium thiosulfate (25 ml) was added and the mixture was poured into saturated sodium thiosulfate (40 ml). The aqueous layer was extracted with ethyl acetate (3×35 ml) and the combined organic layers were washed with brine, dried over magnesium sulfate and concentrated in vacuo. The resultant residue was triturated in dichloromethane:cyclohexane 1:4 to afford the title compound as a yellow solid (0.87 g, 84%). LCMS (method B): RT=3.17 min, M+H+=460.

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