[H-].[Al+3].[Li+].[H-].[H-].[H-].Br[C:8]1[CH:16]=[CH:15][C:14]2[C:10](=[CH:11][N:12]([CH2:17][CH3:18])[N:13]=2)[C:9]=1[C:19](OC)=[O:20].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH2:17]([N:12]1[CH:11]=[C:10]2[C:14]([CH:15]=[CH:16][CH:8]=[C:9]2[CH2:19][OH:20])=[N:13]1)[CH3:18]To a suspension of lithium aluminum hydride (1.09 g, 28.7 mmol) in tetrahydrofuran (60 mL) was added a solution of methyl 5-bromo-2-ethyl-2H-indazole-4-carboxylate (2.03 g, 7.17 mmol) in tetrahydrofuran (15 mL) under nitrogen atmosphere at 0° C., and the mixture was stirred at room temperature for 50 hr. Sodium sulfate decahydrate (10 g) was added under ice-cooling, and the mixture was filtered through celite. The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography (ethyl acetate/hexane=25/75→60/40) to give the title compound (1.14 g, yield 90%).
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