Potassium Phosphate, Tribasic → 1-(4-Cyclopropylpyridin-3-yl)-3-(3-methylbenzofuran-5-yl)imidazolidin-2-one

HRID 523545Notes

Reaction equation

HRID 523545 reaction equation
[CH:1]1([C:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=2[N:10]2[CH2:14][CH2:13][NH:12][C:11]2=[O:15])[CH2:3][CH2:2]1.Br[C:17]1[CH:18]=[CH:19][C:20]2[O:24][CH:23]=[C:22]([CH3:25])[C:21]=2[CH:26]=1.CN[C@@H]1CCCC[C@H]1NC.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[CH:1]1([C:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=2[N:10]2[CH2:14][CH2:13][N:12]([C:17]3[CH:18]=[CH:19][C:20]4[O:24][CH:23]=[C:22]([CH3:25])[C:21]=4[CH:26]=3)[C:11]2=[O:15])[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 123375005-Bromo-3-methyl-1-benzofuranHCID 709820071-(4-Cyclopropylpyridin-3-yl)imidazolidin-2-one

Product 1

HCID 665766471-(4-Cyclopropylpyridin-3-yl)-3-(3-methylbenzofuran-5-yl)imidazolidin-2-oneYield 42.1%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Using analogous reagents and reaction conditions as described in Example 1 above, 1-(4-cyclopropylpyridin-3-yl)imidazolidin-2-one (I-1d: 100 mg, 0.492 mmol) was reacted with 5-bromo-3-methylbenzofuran (125 mg, 0.5904 mmol), 1,4-dioxane (4 mL), copper iodide (10 mg, 0.0492 mmol), trans-N,N′-dimethylcyclohexane-1,2-diamine (7.0 mg, 0.0492 mmol) and potassium phosphate (313 mg, 1.476 mmol) to afford the crude product. Purification by column chromatography on silica gel (1.0% methanol in CHCl3) afforded 69 mg of the product (42% yield).

Workup

  1. customreagents and reaction conditions
  2. customto afford the crude product
  3. customPurification by column chromatography on silica gel (1.0% methanol in CHCl3)

Sources & evidence

ORD record
ord-8ac9f185fc034ca4889dd6c3dcb06369
Source dataset
uspto-grants-2016_05
Patent number
US09339501B2

Reaction notes

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