[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([OH:12])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[N:2]1.Cl[CH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.[C:20]([O-:23])([O-])=O.[Cs+].[Cs+].O>CN1C(=O)CCC1>[O:17]1[CH2:18][CH2:19][CH:14]([N:1]2[C:9]3[C:4](=[CH:5][C:6]([C:10]([O:12][CH:4]4[CH2:3][CH2:20][O:23][CH2:6][CH2:5]4)=[O:11])=[CH:7][CH:8]=3)[CH:3]=[N:2]2)[CH2:15][CH2:16]1A mixture of 1H-indazole-5-carboxylic acid (400 mg, 2.47 mmol), 4-chlorotetrahydro-2H-pyran (1.49 g, 12.33 mmol) and Cs2CO3 (2.41 g, 7.40 mmol) in NMP (5 mL) was irradiated with microwave (180° C., 80 min). The mixture was poured into H2O, extracted with EtOAc, dried over Na2SO4, filtered and concentrated. The residual oil was purified by silica gel column chromatography (30-60% EtOAc in hexane), then the mixture was purified by amino gel column chromatography (0-35% EtOAc in hexane) to give tetrahydro-2H-pyran-4-yl 1-(tetrahydro-2H-pyran-4-yl)-1H-indazole-5-carboxylate (198 mg, 24% yield) as a white solid.
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