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

HRID 2356906

반응식

HRID 2356906 반응식
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.[Ni](Cl)Cl.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=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

참가 물질

8

반응물 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, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 2724937Dichloro(1,1'-(1,3-propanediyl)bis(1,1-diphenylphosphine-kappaP))nickel촉매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-81d7c9f4846449b8a4cbccfc4ac5bf6e
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07759367B2

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