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

HRID 2079884ノート

反応式

HRID 2079884 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 62601Nickel acetate tetrahydrate触媒HCID 887Methanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ea1ca932570a42e184ad6f18c44d109f
出典データセット
uspto-grants-2011_04
特許番号
US07932284B2

反応ノート

読み込み中…