Potassium Carbonate → 6-bromo-1-(4-ethoxyphenyl)-1H-indole

HRID 1948683

Reaction equation

HRID 1948683 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.I[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH3:20])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].N1CCC[C@H]1C(O)=O>CS(C)=O.[Cu]I.O>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH3:20])=[CH:14][CH:13]=2)=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 145742L-ProlineHCID 2207001-Ethoxy-4-iodobenzeneHCID 6764936-Bromoindole

Product 1

HCID 669202456-bromo-1-(4-ethoxyphenyl)-1H-indoleYield 56.4%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A solution of 1.0 g (5 mmol) of 6-bromo-1H-indole, 1.06 g (4.15 mmol) of 4-iodophenetole, 1.45 g of potassium carbonate, 38.1 mg of copper(I) iodide and 42 mg of L-proline in 15 ml of dimethyl sulfoxide is heated at 120° C. for 15 hours. The reaction mixture is then cooled to room temperature, 30 ml of water are added, and the mixture is extracted three times with 20 ml of ethyl acetate each time. After the combined organic phases have been dried over sodium sulfate, the solvent is stripped off in a rotary evaporator, and the crude product is purified by column chromatography on silica gel (n-heptane/ethyl acetate 98:2), giving 0.74 g of 6-bromo-1-(4-ethoxyphenyl)-1H-indole as brownish resin; LC/MS: 317 (M+H).

Workup

  1. extractionthe mixture is extracted three times with 20 ml of ethyl acetate each time
  2. dry with materialAfter the combined organic phases have been dried over sodium sulfate
  3. customthe solvent is stripped off in a rotary evaporator
  4. customthe crude product is purified by column chromatography on silica gel (n-heptane/ethyl acetate 98:2)

Sources & evidence

ORD record
ord-d186617ecc044e7e8fe8929a61fdfec6
Source dataset
uspto-grants-2013_03
Patent number
US08399509B2

Linked notes

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