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

HRID 2079884노트

반응식

HRID 2079884 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 62601Nickel acetate tetrahydrate촉매HCID 887Methanol용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ea1ca932570a42e184ad6f18c44d109f
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07932284B2

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