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

HRID 563398Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 563398
[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

Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3007855ZincchlorideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-23c79fa6a26148e1849251901563fa1f
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08067447B2

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