Diethyl Ether → 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,3-diphenylpropan-1-amine

HRID 218152Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 218152
[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:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH:18]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[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:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH:18]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[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 687038113-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,3-diphenylpropanamide

Produkt 1

HCID 687029583-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,3-diphenylpropan-1-amineAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of the crude 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,3-diphenylpropanamide 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 (65% yield, 3 steps) of 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,3-diphenylpropan-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-2927f95d0ff849ceaa3eaa6d4911f67b
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08198311B2

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