Water → methyl (E)-3-(4-chloro-1-(2-chloro-4-(phenylethynyl)benzyl)-2-methylimidazol-5-yl)-2-propenate

HRID 1828815Notes

Reaction equation

HRID 1828815 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([CH3:22])[N:5]([CH2:13][C:14]2[CH:19]=[CH:18][C:17](I)=[CH:16][C:15]=2[Cl:21])[C:6]=1/[CH:7]=[CH:8]/[C:9]([O:11][CH3:12])=[O:10].[C:23]1([C:29]#[CH:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.O.CCCCCC.C(OCC)(=O)C>C(NC(C)C)(C)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu](I)I>[Cl:1][C:2]1[N:3]=[C:4]([CH3:22])[N:5]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:30]#[C:29][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:16][C:15]=2[Cl:21])[C:6]=1/[CH:7]=[CH:8]/[C:9]([O:11][CH3:12])=[O:10]

Participants

8

Reactant 4

HCID 962WaterHCID 10821PhenylacetyleneHCID 15524214methyl (E)-3-(4-chloro-1-(2-chloro-4-iodobenzyl)-2-methylimidazol-5-yl)-2-propenateHCID 21226206Ethyl acetate hexane

Product 1

HCID 86760100methyl (E)-3-(4-chloro-1-(2-chloro-4-(phenylethynyl)benzyl)-2-methylimidazol-5-yl)-2-propenate

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 7912DiisopropylamineSolvent

Procedure

To a mixture of methyl (E)-3-(4-chloro-1-(2-chloro-4-iodobenzyl)-2-methylimidazol-5-yl)-2-propenate (360 mg), dichlorobis(triphenylphosphine)palladium(II) (28 mg) and copper iodide (7.6 mg) was added a solution of phenylacetylene (326 mg) in diisopropylamine (20 ml) in a nitrogen atmosphere and the mixture was ref luxed under heating for 5 hr. The reaction mixture was allowed to cool. Water was added and the mixture was extracted twice with chloroform. The organic layers were combined, washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The resultant was filtrated under reduced pressure and concentrated to give a crude product. The product was applied to flash silica gel column chromatography (silica gel 10 g) to give methyl (E)-3-(4-chloro-1-(2-chloro-4-(phenylethynyl)benzyl)-2-methylimidazol-5-yl)-2-propenate as brown amorphous (331 mg) from the eluted fraction of hexane/ethyl acetate=5/1–1-1.

Workup

  1. temperatureunder heating for 5 hr
  2. temperatureto cool
  3. extractionthe mixture was extracted twice with chloroform
  4. washwashed with saturated aqueous sodium hydrogencarbonate solution and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationThe resultant was filtrated under reduced pressure
  7. concentrationconcentrated
  8. customto give a crude product

Sources & evidence

ORD record
ord-bc897a336e554a2cb91348830d2b36ed
Source dataset
uspto-grants-2006_06
Patent number
US07060721B1

Reaction notes

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