Sodium borohydride → 5-(trifluoromethyl)-1H-indazole-7-carbaldehyde

HRID 913809노트

반응식

HRID 913809 반응식
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:4]=[C:5]2[C:9](=[C:10]([CH2:12][OH:13])[CH:11]=1)[N:8](COCC[Si](C)(C)C)[N:7]=[CH:6]2.FC(F)(F)C1C=C2C(=C(C=O)C=1)N(COCC[Si](C)(C)C)N=C2.[BH4-].[Na+]>C(O)C>[F:23][C:2]([F:1])([F:22])[C:3]1[CH:4]=[C:5]2[C:9](=[C:10]([CH:12]=[O:13])[CH:11]=1)[NH:8][N:7]=[CH:6]2

참가 물질

5

반응물 3

HCID 4311764Sodium borohydrideHCID 575460585-(Trifluoromethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1h-indazole-7-carbaldehydeHCID 57546212(5-(trifluoromethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-7-yl)methanol

생성물 1

HCID 575462105-(trifluoromethyl)-1H-indazole-7-carbaldehyde

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
0 °C

실험 절차

(5-(Trifluoromethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-7-yl)methanol To a solution of 5-(trifluoromethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole-7-carbaldehyde (1 g, 2.9 mmol) in ethanol (15 mL) at 0° C. was added sodium borohydride (0.055 g, 1.45 mmol). The ice bath was removed and stirring continued for 15 min. The reaction was cooled to 0° C. and quenched by addition of saturated ammonium chloride. The reaction was concentrated to remove most of the ethanol and poured into diethyl ether. The ethereal was washed with water (2×), then brine, dried over magnesium sulfate, and concentrated to give 0.985 g (98%) as an oil which solidified upon standing. 1H-NMR (CDCl3, 500 MHz) δ 8.08 (s, 1H), 8.00 (s, 1H), 7.57 (d, J=1.2 Hz, 1H), 5.96 (s, 2H), 5.07 (s, 2H), 3.53 (m, 2H), 3.34 (bs, 1H), 0.85 (m, 2H), −0.08 (s, 9H); 13C-NMR (CDCl3, 126 MHz) δ 139.0, 135.1, 125.9, 125.3, 124.52 (q, J=272 Hz), 124.51, 124.2 (q,J=33 Hz), 119.3, 80.1, 66.7, 62.6, 17.8, −1.5.

후처리

  1. customThe ice bath was removed
  2. customquenched by addition of saturated ammonium chloride
  3. concentrationThe reaction was concentrated
  4. customto remove most of the ethanol
  5. additionpoured into diethyl ether
  6. washThe ethereal was washed with water (2×)
  7. dry with materialbrine, dried over magnesium sulfate
  8. concentrationconcentrated
  9. customto give 0.985 g (98%) as an oil which

출처 및 근거

ORD 기록
ord-44f8da4e166d4d0db8d75b0e6134e8d3
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08026257B2

반응 노트

불러오는 중…