Tetrahydrofuran → 6-amino-1-isopropyl-3-(3,4,5-trifluoro-phenyl)-1H-indole

HRID 2079884Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2079884
[CH:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([N+:13]([O-])=O)[CH:11]=2)[C:6]([C:16]2[CH:21]=[C:20]([F:22])[C:19]([F:23])=[C:18]([F:24])[CH:17]=2)=[CH:5]1)([CH3:3])[CH3:2].FC1C=CC=C(F)C=1F.O1CCCC1.[BH4-].[Na+]>C(OCC)(=O)C.O.O.O.O.C([O-])(=O)C.[Ni+2].C([O-])(=O)C.CO>[NH2:13][C:10]1[CH:11]=[C:12]2[C:7]([C:6]([C:16]3[CH:21]=[C:20]([F:22])[C:19]([F:23])=[C:18]([F:24])[CH:17]=3)=[CH:5][N:4]2[CH:1]([CH3:3])[CH3:2])=[CH:8][CH:9]=1

Komponenten

8

Edukt 4

HCID 8028TetrahydrofuranHCID 151471,2,3-TrifluorobenzeneHCID 4311764Sodium borohydrideHCID 574421991-isopropyl-6-nitro-3-(3,4,5-trifluoro-phenyl)-1H-indole

Produkt 1

HCID 574421936-amino-1-isopropyl-3-(3,4,5-trifluoro-phenyl)-1H-indole

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 62601Nickel acetate tetrahydrateKatalysatorHCID 887MethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Method H Combine 1-isopropyl-6-nitro-3-(3,4,5-trifluoro-phenyl)-1H-indole (4, R1=i-Pr, R3=3,4,5-trifluoro-benzene) (136.1 mg, 0.41 mmol), nickel(II) acetate tetrahydrate (204 mg, 0.82 mmol), tetrahydrofuran (2.5 mL) and methanol (2.5 mL) in a 50 mL flask. Add sodium borohydride (62 mg, 1.64 mmol) in small portions. Once gas evolution is complete quench the reaction with saturated aqueous ammonium chloride (5 mL), dilute with ethyl acetate (10 mL), and separate the layers. Wash the organic layer with saturated aqueous sodium bicarbonate (5 mL), water (5 mL), brine (5 mL), dry (Na2SO4), filter and concentrate. This material may be used without further purification in the following preparation.

Aufarbeitung

  1. customOnce gas evolution is complete quench
  2. customthe reaction with saturated aqueous ammonium chloride (5 mL)
  3. customseparate the layers
  4. washWash the organic layer with saturated aqueous sodium bicarbonate (5 mL), water (5 mL), brine (5 mL)
  5. dry with materialdry (Na2SO4)
  6. filtrationfilter
  7. concentrationconcentrate
  8. customThis material may be used without further purification in the following preparation

Quellen und Nachweise

ORD-Eintrag
ord-ea1ca932570a42e184ad6f18c44d109f
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07932284B2

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