Potassium Carbonate → 1-(5-Fluoro-3-methyl-benzo[b]thiophen-2-yl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one

HRID 80056Notes

Reaction equation

HRID 80056 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[S:19][C:18]2[CH:20]=[CH:21][C:22]([F:24])=[CH:23][C:17]=2[C:16]=1[CH3:25].N[C@@H]1CCCC[C@H]1N.C(=O)([O-])[O-].[K+].[K+]>[Cu](I)I.O1CCOCC1>[F:24][C:22]1[CH:21]=[CH:20][C:18]2[S:19][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])=[C:16]([CH3:25])[C:17]=2[CH:23]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 438061,2-Diaminocyclohexane, trans-HCID 596361701-(4-Methylpyridin-3-yl)imidazolidin-2-oneHCID 667212022-Bromo-5-fluoro-3-methylbenzo[b]thiophene

Product 1

HCID 596361971-(5-Fluoro-3-methyl-benzo[b]thiophen-2-yl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-oneYield 60.45%

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: 79.79 mg, 0.4508 mmol) was reacted with 2-bromo-5-fluoro-3-methyl-benzo[b]thiophene (110 mg, 0.4508 mmol), 1,4-dioxane (5 mL), copper iodide (8.58 mg, 0.04508 mmol), trans-1,2-diamino cyclohexane (15.48 mg, 0.1352 mmol) and potassium carbonate (124.6 mg, 0.9016 mmol) to afford the crude product. Purification by column chromatography on silica gel (1% MeOH in chloroform) afforded 84 mg of the product (60.45% yield).

Workup

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

Sources & evidence

ORD record
ord-284b1e01988e434ea7fa8cb4e5e2b2c3
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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