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

HRID 898526Notes

Reaction equation

HRID 898526 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

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

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-6b503742cda149c79f0bc141fe7bb514
Source dataset
uspto-grants-2008_04
Patent number
US07351719B2

Reaction notes

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