Bromotrimethylsilane → 4-(4-Bromo-7-chloropyrazolo[4,3-c]pyridin-2-yl)-3,5-dichlorobenzonitrile

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A mixture of 3,5-dichloro-4-(4,7-dichloropyrazolo[4,3-c]pyridin-2-yl)benzonitrile (250 mg, 0.70 mmol) and bromotrimethylsilane (0.462 mL, 3.50 mmol) in propionitrile (4.0 mL) was heated under reflux for 4 hours. The resultant mixture was cooled and concentrated under reduced pressure. The residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The layers were separated and the organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated to afford the title compound as a beige solid (273 mg, 97% yield). 1H NMR (400 MHz, CDCl3): δ 8.30 (s, 1H), 8.16 (s, 1H), 7.85 (s, 2H).

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