Acetonitrile → 1-(2-diethylamino-ethyl)-2,3-dihydro-1H-indol-5-ylamine

HRID 898526ノート

反応式

HRID 898526 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1Cl.[CH2:12]([N:14]([CH2:17][CH3:18])[CH2:15][CH3:16])[CH3:13].[C:19](#[N:21])[CH3:20]>[Cu]I>[CH2:12]([N:14]([CH2:17][CH3:18])[CH2:15][CH2:16][N:21]1[C:2]2[C:3](=[CH:4][C:5]([NH2:8])=[CH:6][CH:7]=2)[CH2:20][CH2:19]1)[CH3:13]

参加物

5

反応物 3

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 346671-Bromo-2-chloro-4-nitrobenzene

生成物 1

HCID 284189531-(2-diethylamino-ethyl)-2,3-dihydro-1H-indol-5-ylamine

試薬・触媒・溶媒 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒

実験手順

Under a nitrogen atmosphere 12.5 mL (0.090 mol) of 3-N,N-diethylamino-propyne was added to 25.00 g (0.106 mol) of 4-bromo-3-chloro-nitrobenzene, 43.7 mL (0.315 mol) of triethylamine, 10.40 g (0.009 mol) of tetrakis[triphenylphosphine]-palladium(II) and 1.71 g (0.009 mol) of copper(I)-iodide in 250 mL acetonitrile and the mixture was refluxed for 18 hours. The reaction mixture was evaporated down i. vac., combined with EtOAc and the organic phase was washed with water. The org. phase was evaporated down i. vac. and the residue was purified by column chromatography (silica gel, petroleum ether/EtOAc 10:0→4:1) followed by column chromatography (silica gel, dichloromethane).

後処理

  1. temperaturethe mixture was refluxed for 18 hours
  2. customThe reaction mixture was evaporated down i
  3. washthe organic phase was washed with water
  4. customphase was evaporated down i
  5. customand the residue was purified by column chromatography (silica gel, petroleum ether/EtOAc 10:0→4:1)

出典と根拠

ORDレコード
ord-6b503742cda149c79f0bc141fe7bb514
出典データセット
uspto-grants-2008_04
特許番号
US07351719B2

反応ノート

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