Potassium Carbonate → 1-(3-Methyl-benzofuran-5-yl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one

HRID 80053Notes

Reaction equation

HRID 80053 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N:8]1[CH2:12][CH2:11][NH:10][C:9]1=[O:13].Br[C:15]1[CH:16]=[CH:17][C:18]2[O:22][CH:21]=[C:20]([CH3:23])[C:19]=2[CH:24]=1.N[C@@H]1CCCC[C@H]1N.C(=O)([O-])[O-].[K+].[K+]>[Cu](I)I.O1CCOCC1>[CH3:23][C:20]1[C:19]2[CH:24]=[C:15]([N:10]3[CH2:11][CH2:12][N:8]([C:3]4[CH:4]=[N:5][CH:6]=[CH:7][C:2]=4[CH3:1])[C:9]3=[O:13])[CH:16]=[CH:17][C:18]=2[O:22][CH:21]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 438061,2-Diaminocyclohexane, trans-HCID 123375005-Bromo-3-methyl-1-benzofuranHCID 596361701-(4-Methylpyridin-3-yl)imidazolidin-2-one

Product 1

HCID 498719671-(3-Methyl-benzofuran-5-yl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-oneYield 30.76%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Using the same reaction conditions as in Example 14, 1-(4-methyl-pyridin-3-yl)-imidazolidin-2-one (I-14b: 105 mg, 0.8465 mol) was reacted with 5-bromo-3-methyl-benzofuran (197 mg, 0.9311 mmol), 1,4-dioxane (10 mL), copper iodide (20 mg), trans-1,2-diamino cyclohexane (40 mg) and potassium carbonate (359 mg, 1.6930 mmol) to afford the crude product. Purification by column chromatography on silica gel (2% MeOH in chloroform) afforded 80 mg of the product (30.76% yield).

Workup

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (2% MeOH in chloroform)

Sources & evidence

ORD record
ord-2a06b3b7de144a5a842c3947d7373962
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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