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Lithium diisopropylamide → 1-Allyl-4-bromo-5-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-pyrazole-3-carbonitrile

HRID 244480
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 244480
[CH2:1]([N:4]1[CH:8]=[C:7]([Br:9])[C:6]([C:10]#[N:11])=[N:5]1)[CH:2]=[CH2:3].C([N-]C(C)C)(C)C.[Li+].[F:20][C:21]([F:41])([F:40])[C:22]([C:24]1[CH:25]=[C:26]2[C:30](=[CH:31][CH:32]=1)[N:29]([C:33]1[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=1)[N:28]=[CH:27]2)=[O:23]>C1COCC1>[CH2:1]([N:4]1[C:8]([C:22]([C:24]2[CH:25]=[C:26]3[C:30](=[CH:31][CH:32]=2)[N:29]([C:33]2[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=2)[N:28]=[CH:27]3)([OH:23])[C:21]([F:40])([F:20])[F:41])=[C:7]([Br:9])[C:6]([C:10]#[N:11])=[N:5]1)[CH:2]=[CH2:3]
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Komponenten

5

Edukt 3

HCID 2724682Lithium diisopropylamideHCID 579432692,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanoneHCID 594372421-allyl-4-bromo-1H-pyrazole-3-carbonitrile

Produkt 1

HCID 594372571-Allyl-4-bromo-5-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-pyrazole-3-carbonitrileAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel
2×

Versuchsvorschrift

To a chilled (−78° C.) solution of 1-allyl-4-bromo-1H-pyrazole-3-carbonitrile (116 mg, 0.550 mmol) in dry THF (2 mL) was added lithium diisopropylamide (367 μL, 1.5 M solution in hexanes, 0.55 mmol). After 5 minutes, a chilled (−78° C.) solution of 2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanone (154 mg, 0.500 mmol) in 2 mL of THF was added. After 15 minutes, the mixture was warmed to room temperature, quenched with 10 mL of saturated aqueous sodium bicarbonate and extracted with three 10 mL portions of ethyl ether. The combined organic layers were washed with 10 mL of brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was chromatographed on SiO2 (0-50% ethyl acetate in hexanes, gradient) to afford 213 mg (82%) of the title product. MS m/z 520.19/522.20 (M+).

Aufarbeitung

  1. additionwas added
  2. waitAfter 15 minutes
  3. customquenched with 10 mL of saturated aqueous sodium bicarbonate
  4. extractionextracted with three 10 mL portions of ethyl ether
  5. washThe combined organic layers were washed with 10 mL of brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was chromatographed on SiO2 (0-50% ethyl acetate in hexanes, gradient)

Quellen und Nachweise

ORD-Eintrag
ord-7afe47646cf64829ab7482b98245c369
Quelldatensatz
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08658637B2

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