C[Si]([Br:5])(C)C.[Cl:6][C:7]1[CH:8]=[C:9]([CH:12]=[C:13]([Cl:25])[C:14]=1[C:15]1[S:16][C:17]2[C:18](Cl)=[N:19][CH:20]=[CH:21][C:22]=2[N:23]=1)[C:10]#[N:11].C(=O)([O-])[O-].[K+].[K+].C(Cl)Cl>C(#N)CC>[Br:5][C:18]1[C:17]2[S:16][C:15]([C:14]3[C:7]([Cl:6])=[CH:8][C:9]([C:10]#[N:11])=[CH:12][C:13]=3[Cl:25])=[N:23][C:22]=2[CH:21]=[CH:20][N:19]=1Trimethylsilylbromide (0.23 mL, 1.74 mmol) was added to a stirred solution of 3,5-dichloro-4-(4-chloro-thiazolo[5,4-c]pyridine-2-yl)-benzonitrile (295 mg, 0.87 mmol) in propionitrile (11 mL) and the mixture heated at 90° C. for 48 hours. The reaction mixture was allowed to cool and poured onto a mixture of saturated aqueous potassium carbonate solution and ice. DCM was added and the organic phase was separated, dried over Na2SO4 and concentrated to dryness under reduced pressure to give the desired compound as a white solid (322 mg, 96% yield). 1H NMR (300 MHz, CDCl3): δ 8.53 (d, J=5.5 Hz, 1H), 8.03-8.00 (m, 1H), 7.80 (s, 2H). LCMS (Method D): RT=4.04 min, m/z: 386 [M+H+].
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