Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]([C:17]([NH:19][CH3:20])=[O:18])=[C:15]3[C:10]([CH:11]=[C:12]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])[C:13]([CH:21]4[CH2:23][CH2:22]4)=[CH:14]3)=[N:9]2)=[CH:4][CH:3]=1.B1(C(C)=C)O[C:32](C)(C)[C:31](C)([CH3:36])O1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>CC([O-])=O.CC([O-])=O.[Pd+2].O.C1(C)C=CC=CC=1>[CH:21]1([C:13]2[C:12]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])=[CH:11][C:10]3[C:15](=[C:16]([C:17]([NH:19][CH3:20])=[O:18])[N:8]([C:5]4[CH:6]=[CH:7][C:2]([C:31]([CH3:36])=[CH2:32])=[CH:3][CH:4]=4)[N:9]=3)[CH:14]=2)[CH2:23][CH2:22]12-(4-bromophenyl)-5-cyclopropyl-N-methyl-6-[(methylsulfonyl)amino]-2H-indazole-3-carboxamide (i) (30 mg, 0.065 mmol), 2-isopropenylboronic acid pinacol ester (37 μL, 0.20 mmol), potassium phosphate (55 mg, 0.26 mmol), tricyclohexylphosphine (3.5 mg, 0.013 mmol) and Pd(OAc)2 (2.1 mg, 0.0094 mmol) had degassed toluene (1 mL) and water (0.1 mL) added and the reaction was heated at 95° C. under argon for 5 h. The reaction mixture was concentrated to dryness and the residue was suspended in DMSO (1 mL), centrifuged, supernatant removed and purified by reverse phase flash column chromatography eluting with ACN/water (0-40-100%) affording 5-cyclopropyl-N-methyl-6-[(methylsulfonyl)amino]-2-[4-(prop-1-en-2-yl)phenyl]-2H-indazole-3-carboxamide (ii) as a white solid (10 mg, 27%).
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