FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][N:14]2[C:22]3[C:17](=[C:18]([NH:23][C:24]([C:26]4[N:30]5[CH:31]=[CH:32][CH:33]=[CH:34][C:29]5=[N:28][CH:27]=4)=[O:25])[CH:19]=[CH:20][CH:21]=3)[C:16]([CH2:35][CH3:36])=[N:15]2)[N:8]=1)(=O)=O.[B-](F)(F)(F)[CH:40]=[CH2:41].[K+].C(N(CC)CC)C>CC(O)C.C1COCC1>[CH2:35]([C:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][C:18]=2[NH:23][C:24]([C:26]2[N:30]3[CH:31]=[CH:32][CH:33]=[CH:34][C:29]3=[N:28][CH:27]=2)=[O:25])[N:14]([CH2:13][C:9]2[CH:10]=[CH:11][CH:12]=[C:7]([CH:40]=[CH2:41])[N:8]=2)[N:15]=1)[CH3:36]To 6-((3-ethyl-4-(imidazo[1,2-a]pyridine-3-carboxamido)-1H-indazol-1-yl)methyl)pyridin-2-yl trifluoromethanesulfonate (100 mg, 0.184 mmol) in IPA/THF (3 mL/1 mL) was added potassium trifluoro(vinyl)borate (36.9 mg, 0.275 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (15.0 mg, 0.0184 mmol) and triethylamine (37.2 mg, 0.367 mmol). The reaction mixture was sealed and heated to 80° C. for 16 hours. The mixture was cooled to ambient temperature and concentrated under reduce pressure. The residue was filtered through a plug of silica gel washing with EtOAc. The solution was concentrated to give the product (72 mg).
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