Sodium borohydride → (7-Methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)methanol
Reaction equation
[CH3:1][C:2]1[C:10]2[C:6](=[CH:7][N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[N:9]=2)[CH:5]=[C:4]([CH:19]=[O:20])[CH:3]=1.[BH4-].[Na+]>C(O)C>[CH3:1][C:2]1[C:10]2[C:6](=[CH:7][N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:17])([CH3:16])[CH3:18])[N:9]=2)[CH:5]=[C:4]([CH2:19][OH:20])[CH:3]=1Participants
Procedure
To a solution of 7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazole-5-carbaldehyde (150 mg, 0.516 mmol) in ethanol (4 mL) at room temperature was added sodium borohydride (19.5 mg, 0.516 mmol). The reaction was stirred at room temperature for 20 min, cooled to 0° C., and quenched by the cautious addition of saturated ammonium chloride. The reaction was poured into diethyl ether and washed with water (2×), then brine, dried over magnesium sulfate, and concentrated to give 139 mg (92%) as an oil. 1H-NMR (CDCl3, 500 MHz) δ 7.97 (s, 1H), 7.38 (s, 1H), 7.01 (s, 1H), 5.65 (s, 2H), 4.64 (s, 2H), 3.58 (m, 2H), 2.57 (s, 3H), 2.51 (bs, 1H), 0.89 (m, 2H), −0.07 (s, 9H); 13C NMR (126 MHz, CDCl3) δ ppm 148.9, 135.1, 128.2, 125.5, 122.9, 121.7, 115.4, 81.5, 67.2, 65.6, 17.7, 17.1, −1.5.
Workup
- temperaturecooled to 0° C.
- customquenched by the cautious addition of saturated ammonium chloride
- additionThe reaction was poured into diethyl ether
- washwashed with water (2×)
- dry with materialbrine, dried over magnesium sulfate
- concentrationconcentrated
- customto give 139 mg (92%) as an oil
Sources & evidence
- ORD record
- ord-f6651d761e424ed4a835279a3af694c2
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08026257B2
Reaction notes
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