Diethyl Ether → 2-((1-(4-fluorophenyl)-1H-indazol-5-yl)(phenyl)methyl)butan-1-amine

HRID 218144Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 218144
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([CH:17]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH:18]([CH2:22][CH3:23])[C:19]([NH2:21])=O)=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)C>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([CH:17]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH:18]([CH2:22][CH3:23])[CH2:19][NH2:21])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 3283Diethyl EtherHCID 21226445Aluminium lithium hydrideHCID 687066063-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2-ethyl-3-phenylpropanamide

Produkt 1

HCID 687056882-((1-(4-fluorophenyl)-1H-indazol-5-yl)(phenyl)methyl)butan-1-amineAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of the crude 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2-ethyl-3-phenylpropanamide in anhydrous THF (10 mL) was added 1.0M lithium aluminum hydride in diethyl ether (2.0 mL, 2.0 mmol) portionwise at RT under nitrogen. After stirring at RT for 24 hr, the mixture was carefully quenched with MeOH, poured into brine (100 mL), extracted with ethyl acetate (2×100 mL), dried (Na2SO4) and concentrated to give 50 mg (88% yield, 3 steps) of 2-((1-(4-fluorophenyl)-1H-indazol-5-yl)(phenyl)methyl)butan-1-amine.

Aufarbeitung

  1. customthe mixture was carefully quenched with MeOH
  2. additionpoured into brine (100 mL)
  3. extractionextracted with ethyl acetate (2×100 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-96b3f1e9148f47b58ded53d976510995
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08198311B2

Notizen zur Reaktion

Wird geladen…