Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]3[N:12](S(C4C=CC(C)=CC=4)(=O)=O)[C:13]4[C:18]([CH:19]=3)=[CH:17][C:16]([O:20][CH3:21])=[C:15]([O:22][CH3:23])[CH:14]=4)=[CH:9][N:10]=2)[N:7]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.[C:76](=[O:79])([O-])[O-].[K+].[K+].CO[C:84]1[CH:85]=[C:86]([CH:88]=[CH:89][C:90]=1[O:91][CH3:92])[NH2:87]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:21][O:20][C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][C:15]=1[O:22][CH3:23])[NH:12][C:11]([C:8]1[N:6]3[N:7]=[C:2]([NH:87][C:86]4[CH:88]=[CH:89][C:90]([O:91][CH3:92])=[C:84]([O:79][CH3:76])[CH:85]=4)[CH:3]=[CH:4][C:5]3=[N:10][CH:9]=1)=[CH:19]2To a solution of 6-chloro-3-(5,6-dimethoxy-1-tosyl-1H-indol-2-yl)imidazo[1,2-b]pyridazine (68 mg, 0.141 mmol, 1.0 equiv), xantphos (16 mg, 0.0282 mmol, 0.2 equiv), palladium acetate (3 mg, 0.0141 mmol, 0.1 equiv), and potassium carbonate (389 mg, 2.82 mmol, 20 equiv) in dioxane (5.0 mL) was added 3,4-dimethoxyaniline (24 mg, 0.155 mmol, 1.1 equiv) and heated to 110° C. for 2 h. Purification by column chromatography using 2% methanol in dichloromethane elution gave 20 mg of the yellow solid.
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