[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH2:11][CH2:12][CH3:13])[N:8]=[C:7]2[C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1.C(N(CC)C(C)C)(C)C.[C:30](Cl)(=[O:33])[CH2:31][CH3:32].O>C(Cl)Cl>[C:30]([O:20][C:17]1[CH:16]=[CH:15][C:14]([C:7]2[C:6]3[C:10](=[C:2]([Cl:1])[CH:3]=[CH:4][CH:5]=3)[N:9]([CH2:11][CH2:12][CH3:13])[N:8]=2)=[CH:19][CH:18]=1)(=[O:33])[CH2:31][CH3:32]To a solution of 4-(7-chloro-1-propyl-1H-indazol-3-yl)phenol (0.100 g, 0.35 mmol) and N,N-diisopropylethyl amine (0.5 g, 0.38 mmol) in CH2Cl2 (5 mL) was added dropwise propionyl chloride (0.035 g, 0.38 mmol). The solution was allowed to stir overnight at room temperature. Water was added and the solution was extracted with CH2Cl2. The organic layer was washed with brine and dried (MgSO4). The product was purified by flash chromatography (5/1 hexane/ethyl acetate) to yield a white solid (0.106 g, 88%).
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