Cesium carbonate → 1-(5-Bromo-3-pyridinyl)-2-pyrrolidinone

HRID 340448노트

반응식

HRID 340448 반응식
C(=O)([O-])[O-].[Cs+].[Cs+].[NH:7]1[CH2:11][CH2:10][CH2:9][C:8]1=[O:12].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.[Br:55][C:56]1[CH:57]=[N:58][CH:59]=[C:60](Br)[CH:61]=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O.O1CCOCC1>[Br:55][C:56]1[CH:61]=[C:60]([N:7]2[CH2:11][CH2:10][CH2:9][C:8]2=[O:12])[CH:59]=[N:58][CH:57]=1

참가 물질

8

반응물 4

HCID 10796Cesium carbonateHCID 120252-PyrrolidoneHCID 693693,5-DibromopyridineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)

생성물 1

HCID 686194601-(5-Bromo-3-pyridinyl)-2-pyrrolidinone수율 44.2%

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

Cesium carbonate (213 mg), pyrrolidin-2-one (45 mg), Xantphos (76 mg), and Pd2(dba)3 (60 mg) were added to a 1,4-dioxane (4 ml) solution containing 3,5-dibromopyridine (100 mg) in a nitrogen atmosphere, followed by reflux for 4 hours. The reaction mixture was adjusted to room temperature and water was added, followed by extraction with ethyl acetate. The resultant was washed with saturated saline and dried over anhydrous sodium sulfate. Then, the solvent was distilled away under reduced pressure, the obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=3:1 to 1:1), and a white solid of 1-(5-bromopyridin-3-yl)pyrrolidin-2-one (45 mg) was thus obtained.

후처리

  1. temperatureby reflux for 4 hours
  2. customwas adjusted to room temperature
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe resultant was washed with saturated saline
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThen, the solvent was distilled away under reduced pressure
  7. customthe obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=3:1 to 1:1)

출처 및 근거

ORD 기록
ord-117c135a6fd74339ac2a33d72b24d8e9
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895585B2

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