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

HRID 1784862ノート

反応式

HRID 1784862 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-c4902999dbd14def8e1e030623f1b029
出典データセット
uspto-grants-2009_03
特許番号
US07504401B2

反応ノート

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