Benzo(b)thiophene, 3-bromo- → N-(1-Benzo[b]thiophen-3-ylmethyl-2,2,2-trifluoroethyl)-2,4,6-trimethylbenzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

A mixture of 9 mg (2.20 mmol) of magnesium powder, 79 mg (0.37 mmol) of 3-bromobenzo[b]thiophene, 8 mg (0.04 mmol) of copper (I) iodide, and 50 mg (0.17 mmol) of 2-trifluoromethyl-1-(2,4,6-trimethylbenzenesulfonyl)aziridine in 1 mL of THF was warmed at 80° C. in a sealed tube. After 30 minutes, the reaction was quenched with 7 mL of saturated aqueous ammonium chloride solution and extracted with three 7 mL portions of ethyl acetate. The combined organic layers were washed with two 5 mL portions of brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude material was chromatographed on silica gel using dichloromethane-hexanes (1:1) to load the sample and then eluting with dichloromethane-hexanes (1:1, then 75:25). The material from the column was triturated with ether-hexanes to afford 17 mg (23%) of the title compound as a white solid which is consistent with the desired product. MS: m/z 428.51 (M+1).

Provenance & Evidence