o-Toluenesulfonyl chloride → HCID 57537464, compound

Participants

Reaction Conditions

Reaction Steps

3-(4-Chloro-1H-pyrrolo[2,3-b]pyridin-5-yl)-N,N-dimethyl-benzamide (148 mg, 0.5 mmol) was dissolved in 3.5 mL acetone, and N-iodosuccinimide (133 mg, 0.6 mmol) was added. The suspension was stirred for 1 h at 23° C., diluted with water and sodium thiosulfate solution, filtered, and washed with water. The yellow powder was dissolved in 5 mL dry DMF and sodium hydride (30 mg, 0.75 mmol) was added. After the gas evolution subsided (10 min), toluenesulfonyl chloride (141 mg, 0.75 mmol) was added. The mixture was stirred at 60° C. for 12 h and quenched with saturated ammonium chloride solution. The suspension was filtered and washed with water to afford 3-[4-Chloro-3-iodo-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-benzamide as a light brown solid (310 mg, 0.49 mmol, quantitative). 1H NMR (500 MHz, DMSO-d6) δ 8.38 (s, 1H), 8.28 (s, 1H), 8.05 (m, 2H), 7.44-7.56 (m, 6H), 2.97 (bs, 3H), 2.93 (bs, 3H), 2.36 (s, 3H). MS: m/z 580.2 (M+H).

Provenance & Evidence