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Sodium hydride → (R)-1-(3-{2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}indol-1-yl)propan-2-ol

HRID 244424
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 244424
[F:1][C:2]([F:31])([F:30])[C:3]([C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[N:19]([C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1)[N:18]=[CH:17]2)([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1)[OH:4].[H-].[Na+].[H][H].[CH2:36]1[O:39][C@@H:37]1[CH3:38]>C1COCC1.O>[F:31][C:2]([F:30])([F:1])[C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([CH2:36][C@H:37]([OH:39])[CH3:38])[CH:6]=1)([C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[N:19]([C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1)[N:18]=[CH:17]2)[OH:4]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 24758Sodium hydrideHCID 146261(R)-1,2-EpoxypropaneHCID 579433222,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-(1H-indol-3-yl)ethanolHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 59437208(R)-1-(3-{2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}indol-1-yl)propan-2-olAusbeute 47,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a room temperature solution of 100 mg (0.23 mmol) of 2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-(1H-indol-3-yl)ethanol in THF was added 20.0 mg (0.50 mmol) of 60% NaH in mineral oil. After hydrogen evolution ceased, 14.5 mg (0.25 mmol) of (R)-(+)-propylene oxide was added. The reaction was then warmed at 60° C. for 5 hours. The reaction was then cooled to room temperature and diluted with water and extracted with ether. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The crude residue was purified by flash chromatography (20-40% ethyl acetate in hexanes). The major fractions were combined and concentrated to provide 53 mg (46.6%) of the title compound. MS m/z 484.47 (MH+).

Aufarbeitung

  1. temperatureThe reaction was then cooled to room temperature
  2. extractionextracted with ether
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified by flash chromatography (20-40% ethyl acetate in hexanes)
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d38917c0815b4762a6161b1dc61302f2
Quelldatensatz
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08658637B2

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