Potassium Carbonate → 1-(1-Ethyl-1H-indol-5-yl)-3-pyridin-3-yl-imidazolidin-2-one

HRID 2383707Notes

Reaction equation

HRID 2383707 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[CH2:11][CH2:10][NH:9][C:8]2=[O:12])[CH:2]=1.Br[C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[N:19]([CH2:23][CH3:24])[CH:18]=[CH:17]2.N[C@@H]1CCCC[C@H]1N.C(=O)([O-])[O-].[K+].[K+]>[Cu](I)I.O1CCOCC1>[CH2:23]([N:19]1[C:20]2[C:16](=[CH:15][C:14]([N:9]3[CH2:10][CH2:11][N:7]([C:3]4[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=4)[C:8]3=[O:12])=[CH:22][CH:21]=2)[CH:17]=[CH:18]1)[CH3:24]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 438061,2-Diaminocyclohexane, trans-HCID 43839595-Bromo-1-ethyl-1H-indoleHCID 148342041-(Pyridin-3-yl)imidazolidin-2-one

Product 1

HCID 596361531-(1-Ethyl-1H-indol-5-yl)-3-pyridin-3-yl-imidazolidin-2-oneYield 49.33%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Using the same reaction conditions as in Example 1, 1-pyridin-3-yl-imidazolidin-2-one (I-1b: 200 mg, 1.226 mmol) was reacted with 5-bromo-1-ethyl-1H-indole (274 mg, 1.226 mmol), 1,4-dioxane (10 mL), copper iodide (23.3 mg, 0.1226 mmol), trans-1,2-diamino cyclohexane (20.99 mg, 1.839 mmol) and potassium carbonate (338 mg, 2.452 mmol) to afford the crude product. Purification by column chromatography on silica gel (30% ethylacetate in hexane), afforded 185 mg of the product (49.33% yield).

Workup

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (30% ethylacetate in hexane)

Sources & evidence

ORD record
ord-9e667ec639d64cc2ae74605fd5a769dc
Source dataset
uspto-grants-2012_09
Patent number
US08263635B2

Reaction notes

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