[Br:1][C:2]1[CH:3]=[C:4]([C:12]([NH:14][C:15]2[C:16](Cl)=[N:17][C:18]([Cl:22])=[CH:19][C:20]=2[CH3:21])=[O:13])[C:5]([NH:8][CH:9]2[CH2:11][CH2:10]2)=[N:6][CH:7]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].C1COCC1>N1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[N:6][C:5]2[N:8]([CH:9]3[CH2:11][CH2:10]3)[C:16]3[N:17]=[C:18]([Cl:22])[CH:19]=[C:20]([CH3:21])[C:15]=3[NH:14][C:12](=[O:13])[C:4]=2[CH:3]=1A solution of 5-bromo-2-(cyclopropylamino)-N-(2,6-dichloro-4-methyl-3-pyridinyl)-3-pyridinecarboxamide (105 mg, 0.254 mmol) in pyridine (3.0 mL) was heated to 50° C. while a 1 M solution of NaHMDS in THF (0.53 mL, 0.53 mmol) was added. The resulting solution was stirred at 50° C. for 3 h. The reaction was quenched with aqueous saturated NH4Cl, diluted with water and extracted with EtOAc (3×). The combined organic extracts were washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure. The resulting residue was purified via flash chromatography (hexane:EtOAc, 7:3) to give the title compound (32 mg, 33% yield).
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