Ammonia → 3-(1-Adamantyl)-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one

HRID 229685

반응식

HRID 229685 반응식
Br[C:2]1[C:3](=[O:20])[N:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:7]=1.[Br-].[C:22]12([Zn+])[CH2:31][CH:26]3[CH2:27][CH:28]([CH2:30][CH:24]([CH2:25]3)[CH2:23]1)[CH2:29]2.N>O1CCCC1.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Fe].[Cu]I>[C:22]12([C:2]3[C:3](=[O:20])[N:4]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH:5]=[C:6]([C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=4)[CH:7]=3)[CH2:31][CH:26]3[CH2:27][CH:28]([CH2:30][CH:24]([CH2:25]3)[CH2:23]1)[CH2:29]2

참가 물질

7

반응물 3

HCID 222AmmoniaHCID 223190653-Bromo-1-phenyl-5-(pyridin-2-yl)-1,2-dihydropyridin-2-oneHCID 178419756HCID 178419756, 화합물

생성물 1

HCID 223192453-(1-Adamantyl)-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178477754HCID 178477754, 화합물촉매HCID 8028Tetrahydrofuran용매

실험 절차

40 mg of 3-bromo-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one was dissolved in 10 ml of tetrahydrofuran. To the mixture were added 5 mg of [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium (II) and 1.2 mg of copper (I) iodide. While stirring the mixture at room temperature in nitrogen atmosphere overnight, 0.4 ml of 1-adamantyl zinc bromide (0.5M tetrahydrofuran solution) was added dropwise thereinto. After stirring in nitrogen atmosphere overnight, an aqueous ammonia 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 (hexane/ethyl acetate system), to give 12 mg of the title compound.

후처리

  1. additionwas added dropwise
  2. extractionby extracting with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified by silica gel chromatography (hexane/ethyl acetate system)

출처 및 근거

ORD 기록
ord-fb7248b1c00c4b6f9ac0e0edad1c6ba7
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07563811B2

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