[CH:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[N:9][NH:10]2)=[CH:6][C:5]=1[OH:13])([CH3:3])[CH3:2].[C@@H]1(N)CCCC[C@H]1N.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[F:30][C:31]1[CH:36]=[CH:35][C:34](I)=[CH:33][CH:32]=1>O1CCOCC1.CCOC(C)=O.[Cu]I>[F:30][C:31]1[CH:36]=[CH:35][C:34]([N:10]2[C:11]3[C:7](=[CH:6][C:5]([OH:13])=[C:4]([CH:1]([CH3:3])[CH3:2])[CH:12]=3)[CH:8]=[N:9]2)=[CH:33][CH:32]=16-Isopropyl-1H-indazol-5-ol was dissolved in 20 mL dry dioxane in a stainless steel pressure tube. Trans-1,2-cyclohexanediamine (0.35 mL, 2.88 mmol) was added followed by CuI (110 mg, 0.58 mmol) and then K3PO4 2.2 g, 10.4 mmol). After the addition of 4-fluoro-1-iodobenzene (0.7 mL, 6.0 mmol), the reactor was sealed and heated at 100 C for 24 h. The reactor was cooled and the contents were taken up in EtOAc, filtered through a SiO2 plug using EtOAc as the eluent and concentrated in vacuo. The crude product was chromatographed on SiO2 using 1:3 EtOAc/hexanes to give 453 mg (29% yield) of 1-(4-fluorophenyl)-6-isopropyl-1H-indazol-5-ol. MS found: (M+H)+=271.
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