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

HRID 2079884Notes

Reaction equation

HRID 2079884 reaction equation
[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

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 62601Nickel acetate tetrahydrateCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-ea1ca932570a42e184ad6f18c44d109f
Source dataset
uspto-grants-2011_04
Patent number
US07932284B2

Reaction notes

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