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With lithium aluminium tetrahydride; In tetrahydrofuran; at 20.0℃; for 2.0h;
General procedure: 1-Benzyl-7-methyl-1H-indole-6-carboxylic acid methyl ester (100mg, 0.36mmol) obtained from Preparation Example 17-1 was dissolved in tetrahydrofuran (7ml), and lithium aluminium hydride (100mg, 2.63mmol) was added dropwise thereto. The mixture was stirred for 2 hours at room temperature and then water (1ml), 6N sodium hydroxide (2ml) and water (3ml) were added sequentially. Ethyl acetate was added thereto, and the mixture was filtered with Celite. Filtrate was distilled under reduced pressure and separated by column chromatography to obtain the title compound (92mg, 100%).[643] NMR:1H-NMR(500HMz, CDCl3); delta 7.53 (d, 1H), 7.31 (m, 3H), 7.11 (m, 2H), 6.96 (d, 2H), 6.59 (d, 1H), 5.60 (s, 1H), 4.73 (d, 2H), 2.55 (s, 3H), 1.89 (t, 1H)
With lithium aluminium tetrahydride; In tetrahydrofuran; at 0℃; for 1.5h;
A. (l-methy/-lH-indazol-6-yl)methanol [00481] A solution of methyl 1 -methyl- lH-indazole-6-carboxylate (230 mg, 1.21 mmol, PREPARATION 4) in anhydrous THF (4 mL) was cooled to 0 C, L1AIH4 (92 mg, 2.42 mmol) was added in portions below 0 C, and the mixture was then stirred at 0 C for 1.5h, added water: 10% NaOH: water = 0.2 mL: 0.2 mL: 0.6 mL carefully, filtered, and the filtrate was concentrated and purified by silica gel flash column to give 192 mg of crude product which was used directly for next step (98%). [M+H] Calc'd for C9Hi0N2O, 163; Found, 163.
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