[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([NH2:10])[C:4]=2[CH:3]=[N:2]1.I[C:12]1[CH:13]=[C:14]([CH:19]=[CH:20][CH:21]=1)[C:15]([O:17][CH3:18])=[O:16].CN[C@@H]1CCCC[C@H]1NC.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.[Cu]I>[NH2:10][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[CH:3]=[N:2][N:1]2[C:12]1[CH:13]=[C:14]([CH:19]=[CH:20][CH:21]=1)[C:15]([O:17][CH3:18])=[O:16]1H-Indazol-4-amine (81 mg, 0.61 mmol) and methyl 3-iodobenzoate (160 mg, 0.61 mmol) were dissolved in DMF (1 mL) in a microwave tube. Copper (I) iodide (23 mg, 0.12 mmol), trans-N,N′-dimethyl-1,2-cyclohexanediamine (34 mg, 0.24 mmol) and potassium carbonate (169 mg, 1.22 mmol) were added and the mixture heated by microwave (250 W) at 100° C. for 20 minutes. The mixture was filtered through a cartridge, washing with DCM (5 mL) and the filtrate was evaporated to dryness and purified by mass-directed autopreparation. The appropriate fractions were evaporated, dissolved in DCM (10 mL), washed with aqueous sodium bicarbonate, and evaporated to give the title compound (32.7 mg).
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