Ammonium Chloride → 3-(2-Chlorophenyl)-5-cyclohexyl-1-phenyl-1,2-dihydropyridin-2-one

HRID 547722

Reaktionsgleichung

Reaktionsgleichung von HRID 547722
Br[C:2]1[CH:3]=[C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[Cl:21])[C:5](=[O:14])[N:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:7]=1.BrC1C=C(I)C(=O)N([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)C=1.ClC1C=CC=CC=1B(O)O.C1([Mg]Cl)CCCCC1.[Cl-].[NH4+]>O1CCCC1.Cl[Ni]1(Cl)[P](C2C=CC=CC=2)(C2C=CC=CC=2)CCC[P]1(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C:4]1[C:5](=[O:14])[N:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:7]=[C:2]([CH:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)[CH:3]=1

Komponenten

8

Edukt 5

HCID 25517Ammonium ChlorideHCID 27343222-Chlorophenylboronic acidHCID 223189575-Bromo-3-iodo-1-phenylpyridin-2(1H)-oneHCID 223190405-Bromo-3-(2-chlorophenyl)-1-phenyl-1,2-dihydropyridin-2-oneHCID 178478990HCID 178478990, Verbindung

Produkt 1

HCID 223190693-(2-Chlorophenyl)-5-cyclohexyl-1-phenyl-1,2-dihydropyridin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418745HCID 178418745, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

30 mg of 5-bromo-3-(2-chlorophenyl)-1-phenyl-1,2-dihydropyridin-2-one synthesized from 5-bromo-1-phenyl-3-iodo-1,2-dihydropyridin-2-one and 2-chlorophenyl boronic acid in accordance with the method of Referential Example 3 was dissolved in 20 ml of tetrahydrofuran, followed by adding 1 mg of [1,3-bis(diphenylphosphino)propane]nickel (II) chloride. Under stirring in nitrogen atmosphere, 0.1 ml of cyclohexyl magnesium chloride (2.0M ether solution) was added dropwise thereinto. After stirring at room temperature in nitrogen atmosphere overnight, the mixture was heated under reflux for 1 hour. After cooling to room temperature, a saturated aqueous solution of ammonium chloride was added thereto, followed by extracting with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel chromatography (chloroform/methanol system), to give 6 mg of the title compound.

Aufarbeitung

  1. additionwas added dropwise
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 1 hour
  4. temperatureAfter cooling to room temperature
  5. extractionby extracting with ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated
  9. customthe residue was purified by silica gel chromatography (chloroform/methanol system)

Quellen und Nachweise

ORD-Eintrag
ord-cfcde7b60ad24e15b48a7395372ec5b4
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07939549B2

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