Dimethylformamide → 7-Bromo-1,2,3-benzothiadiazole-5-carbonitrile

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Reaction Conditions

Reaction Steps

A mixture of 7-bromo-5-iodo-1,2,3-benzothiadiazole (22 mg, 0.0645 mmol), zinc cyanide (7.58 mg, 0.0645 mmol), Pd(PPh3)4 (7.46 mg, 0.00645 mmol) and DMF (2 mL) was heated to 60° C. for 4 h. The solution was extracted with EtOAc (50 mL), and the organic fraction was washed with saturated aqueous sodium bicarbonate solution (3×50 mL). The organic fraction was adsorbed onto silica gel and purified by ISCO chromatography (3 to 5% EtOAc:heptane) to afford 14 mg (90%) of the title compound as a white solid. 1H NMR (400 MHz, CDCl3): δ 8.03 (d, J=1.0 Hz, 1 H), 8.92 (d, J=1.3 Hz, 1 H).

Provenance & Evidence