[Cl:1][C:2]1[C:3]([N:10]2[CH:20]=[C:13]3[C:14](Cl)=[N:15][CH:16]=[C:17]([F:18])[C:12]3=[N:11]2)=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].[Br:21][Si](C)(C)C>C(#N)CC>[Br:21][C:14]1[C:13]2=[CH:20][N:10]([C:3]3[C:2]([Cl:1])=[CH:9][CH:8]=[CH:7][C:4]=3[C:5]#[N:6])[N:11]=[C:12]2[C:17]([F:18])=[CH:16][N:15]=13-Chloro-2-(4-chloro-7-fluoropyrazolo[4,3-c]pyridin-2-yl)-benzonitrile (890 mg, 2.9 mmol) was suspended in propionitrile (30 mL), under an atmosphere of nitrogen and bromotrimethylsilane (2.0 mL, 15 mmol) was added. The reaction mixture was heated at 110° C. for 3.5 hours. The resultant mixture was cooled to room temperature and 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 under reduced pressure. The residue was triturated with diethyl ether to afford the title compound as a yellow solid (980 mg, 96% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.54 (d, J=2.5 Hz, 1H), 8.25-8.21 (m, 3H), 7.94 (t, J=8.1 Hz, 1H).
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