Sodium Thiosulfate → HCID 57537599, compound

Participants

Reaction Steps

1.117 g (2.59 mmol) of 5-[4-chloro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-nicotinamide was dissolved in 19 ml of anhydrous 1,2-dichloroethane. 1.506 g (6.69 mmol) of N-iodosuccinimide was added and the mixture irradiated in a microwave reactor to 140° C. for 30 minutes. Saturated aqueous solution of sodium thiosulfate was added and the resulting mixture stirred at ambient temperature, then diluted with water and dichloromethane. The aqueous phase was separated and extracted three times with dichloromethane. The combined organic phases were dried over sodium sulfate and evaporated. The resulting crude was purified by flash chromatography on silica gel using a gradient of 10% v/v methanol in ethyl acetate and hexanes to afford 904.7 mg (62%, 1.625 mmol) of (5-[4-chloro-3-iodo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-nicotinamide as a brown oil. 1H-NMR [500 MHz, d6-DMSO] d 8.75 (m, 1H), 8.69 (m, 1H), 8.39 (m, 1H), 8.12 (s, 1H), 8.02 (m, 1H), 5.64 (s, 2H), 3.54 (t, 2H), 3.02 (s, 3H), 3.00 (s, 3H), 0.84 (t, 2H), 0.09 (s, 9H); MS [MH+] m/z: 557.

Provenance & Evidence