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

HRID 340448ノート

反応式

HRID 340448 の反応式
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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-117c135a6fd74339ac2a33d72b24d8e9
出典データセット
uspto-grants-2014_11
特許番号
US08895585B2

反応ノート

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