Silane, (ethenyloxy)trimethyl- → 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-3-methylbutanal

HRID 563398노트

반응식

HRID 563398 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17](O)([CH3:19])[CH3:18])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.C[Si](C)(C)[O:23][CH:24]=[CH2:25]>ClCCl.[Cl-].[Zn+2].[Cl-]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]([CH3:19])([CH3:18])[CH2:23][CH:24]=[O:25])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:6][CH:7]=1

참가 물질

5

반응물 2

HCID 80344Silane, (ethenyloxy)trimethyl-HCID 670058142-(1-(4-fluorophenyl)-1H-indazol-5-yl)propan-2-ol

생성물 1

HCID 866403053-(1-(4-fluorophenyl)-1H-indazol-5-yl)-3-methylbutanal

시약·촉매·용매 2

HCID 3007855Zincchloride촉매HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of 2-(1-(4-fluorophenyl)-1H-indazol-5-yl)propan-2-ol (Example 113(d), 200 mg, 0.74 mmol) and trimethyl(vinyloxy)silane (0.5 mL) in anhydrous dichloromethane (1 mL) was added zinc chloride (1M solution in diethyl ether, 2.2 mL, 2.2 mmol) dropwise at 0° C. under argon. The reaction mixture was stirred at rt for 1.5 hr before being quenched by the addition of saturated aqueous ammonium chloride solution (2 mL). The aqueous layer was separated and extracted with ethyl acetate (2×2 mL). The combined organic layers were dried (Na2SO4), concentrated and purified by silica gel flash chromatography to give 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-3-methylbutanal as a liquid.

후처리

  1. custombefore being quenched by the addition of saturated aqueous ammonium chloride solution (2 mL)
  2. customThe aqueous layer was separated
  3. extractionextracted with ethyl acetate (2×2 mL)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated
  6. custompurified by silica gel flash chromatography

출처 및 근거

ORD 기록
ord-23c79fa6a26148e1849251901563fa1f
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08067447B2

반응 노트

불러오는 중…