N,N'-Dimethylethylenediamine → 1-[3-Bromo-5-(pyridine-3-carbonyl)-phenyl]-pyrrolidin-2-one

HRID 1784862노트

반응식

HRID 1784862 반응식
Br[C:2]1[CH:3]=[C:4]([C:9]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[O:10])[CH:5]=[C:6]([Br:8])[CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CNCCNC.[NH:29]1[CH2:33][CH2:32][CH2:31][C:30]1=[O:34]>[Cu]I.O1CCOCC1>[Br:8][C:6]1[CH:7]=[C:2]([N:29]2[CH2:33][CH2:32][CH2:31][C:30]2=[O:34])[CH:3]=[C:4]([C:9]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[O:10])[CH:5]=1

참가 물질

7

반응물 4

HCID 8070N,N'-DimethylethylenediamineHCID 10796Cesium carbonateHCID 120252-PyrrolidoneHCID 106649193-(3,5-Dibromobenzoyl)pyridine

생성물 1

HCID 574709891-[3-Bromo-5-(pyridine-3-carbonyl)-phenyl]-pyrrolidin-2-one수율 7.2%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 312751,4-Dioxane용매

반응 조건

온도
80 °C

실험 절차

To a nitrogen-flushed tube were added 0.20 grams (0.72 mmol) (3,5-dibromo-phenyl)-pyridin-3-yl-methanone, 0.137 g (0.72 mmol) copper (I) iodide, 0.235 (0.72 mmol) cesium carbonate, 0.063 g (0.72 mmol) N,N′-dimethyl-ethane-1,2-diamine, 0.061 g (0.72 mmol) pyrrolidin-2-one and 5 mL dioxane. The tube was sealed and heated at 80° C. overnight. The reaction mixture was allowed to cool, and was filtered. The volatiles were removed under reduced pressure and the resulting material was chromatographed on silica gel with 2% methanol/chloroform to give 0.018 g of 1-[3-bromo-5-(pyridine-3-carbonyl)-phenyl]-pyrrolidin-2-one. This material was converted to 1-[3-(1H-indol-4-yl)-5-(pyridine-3-carbonyl)-phenyl]-pyrrolidin-2-one as described in Example 75. 1H NMR (400 MHz, CD3OD): δ 9.01 (s, 1H), 8.79 (s, 1H), 8.26-8.31 (m, 2H), 8.06 (s, 1H), 7.86 (s, 1H), 7.62 (s, 1H), 7.42 (d, J=8.0 Hz, 1H), 7.30 (d, J=3.1 Hz, 1H), 7.19 (t, J=7.5 Hz, 1H), 7.14 (d, J=7.2 Hz, 1H), 6.67 (d, J=3.1 Hz, 1H), 4.03 (t, J=7.0 Hz, 2H), 2.63 (t, J=8.1 Hz, 2H), 2.16-2.26 (m, 2H).

후처리

  1. customTo a nitrogen-flushed tube
  2. customThe tube was sealed
  3. temperatureto cool
  4. filtrationwas filtered
  5. customThe volatiles were removed under reduced pressure
  6. customthe resulting material was chromatographed on silica gel with 2% methanol/chloroform

출처 및 근거

ORD 기록
ord-c4902999dbd14def8e1e030623f1b029
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07504401B2

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