Sodium borohydride → (5-Chloro-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-7-yl)methanol

HRID 913913노트

반응식

HRID 913913 반응식
[Cl:1][C:2]1[CH:10]=[C:9]([CH:11]=[O:12])[C:8]2[C:4](=[CH:5][N:6]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[N:7]=2)[CH:3]=1.[BH4-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:10]=[C:9]([CH2:11][OH:12])[C:8]2[C:4](=[CH:5][N:6]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[N:7]=2)[CH:3]=1

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 575462315-Chloro-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazole-7-carbaldehyde

생성물 1

HCID 57546244(5-Chloro-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-7-yl)methanol

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a suspension of 5-chloro-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazole-7-carbaldehyde (3 g, 9.65 mmol) in ethanol (20 mL) at 0° C. was added sodium borohydride (0.183 g, 4.83 mmol). The ice bath was removed and stirring continued for 1 h. The reaction was recooled to 0° C. and quenched by the cautious addition of saturated ammonium chloride. The reaction was concentrated to remove most of the ethanol. The resulting residue was dissolved in water and extracted with diethyl ether (2×). The ethereal was washed with water, then brine, dried over magnesium sulfate, and concentrated to give 3.3 g (quant.) as a viscous oil. 1H-NMR (CDCl3, 500 MHz) δ 8.04 (s, 1H), 7.55 (d, J=1.5 Hz, 1H), 7.19 (d, J=1.2 Hz, 1H), 5.67 (s, 2H), 5.04 (d, J=4.9 Hz, 2H), 3.61 (t, J=8.2 Hz, 2H), 3.31 (m, 1H), 0.92 (t, J=8.2 Hz, 2H), −0.04 (s, 9H); 13C NMR (126 MHz, CDCl3) δ ppm 145.9, 132.4, 128.0, 124.7, 122.7, 122.6, 118.3, 81.9, 67.8, 62.3, 17.9, −1.4. Mass spec.: 313.12 (MH)+.

후처리

  1. customThe ice bath was removed
  2. customwas recooled to 0° C.
  3. customquenched by the cautious addition of saturated ammonium chloride
  4. concentrationThe reaction was concentrated
  5. customto remove most of the ethanol
  6. dissolutionThe resulting residue was dissolved in water
  7. extractionextracted with diethyl ether (2×)
  8. washThe ethereal was washed with water
  9. dry with materialbrine, dried over magnesium sulfate
  10. concentrationconcentrated
  11. customto give 3.3 g (quant.) as a viscous oil

출처 및 근거

ORD 기록
ord-8ae5816577da491c86c8d13071d7223a
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08026257B2

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