1,10-Phenanthroline → 2-Cyclopentyl-N-(2,6-dimethyl-4-pyrrol-1-yl-phenyl)-acetamide

HRID 1820145

反応式

HRID 1820145 の反応式
C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].[NH:39]1[CH:43]=[CH:42][CH:41]=[CH:40]1.Br[C:45]1[CH:50]=[C:49]([CH3:51])[C:48]([NH:52][C:53](=[O:60])[CH2:54][CH:55]2[CH2:59][CH2:58][CH2:57][CH2:56]2)=[C:47]([CH3:61])[CH:46]=1>C1(C)C=CC=CC=1.FC(F)(F)S([O-])(=O)=O.[Cu+2].FC(F)(F)S([O-])(=O)=O>[CH:55]1([CH2:54][C:53]([NH:52][C:48]2[C:47]([CH3:61])=[CH:46][C:45]([N:39]3[CH:43]=[CH:42][CH:41]=[CH:40]3)=[CH:50][C:49]=2[CH3:51])=[O:60])[CH2:59][CH2:58][CH2:57][CH2:56]1

参加物

8

反応物 5

HCID 13181,10-PhenanthrolineHCID 8027PyrroleHCID 10796Cesium carbonateHCID 95417Dibenzylidene acetoneHCID 11507840N-(4-bromo-2,6-dimethyl-phenyl)-2-cyclopentyl-acetamide

生成物 1

HCID 116090672-Cyclopentyl-N-(2,6-dimethyl-4-pyrrol-1-yl-phenyl)-acetamide収率 9%

試薬・触媒・溶媒 2

HCID 2734996copper(II) trifluoromethanesulfonate触媒HCID 1140Toluene溶媒

反応条件

温度
110 °C

実験手順

Dibenzylideneacetone (1.1 mg) and 1,10-phenanthroline (17 mg) were mixed in dry toluene (1 mL) under argon for 5 minutes, followed by addition of copper(II) trifluoromethanesulfonate (1.8 mg), cesium carbonate (35 mg), pyrrole (10 mg) and N-(4-bromo-2,6-dimethyl-phenyl)-2-cyclopentyl-acetamide (1p, 30 mg) and the reaction was heated to 110° C. in a sealed 4 mL vial under argon for 48 hours. The reaction mixture was concentrated in vacuo, sodium hydroxide (2 M, 1.5 mL) was added and the product was extracted with isopropyl acetate (3×1.5 mL). The combined organic phases were dried over magnesium sulfate, concentrated in vacuo and redissolved in dimethyl sulfoxide (0.50 mL) of which 0.25 mL was subjected to preparative LC-MS purification to furnish 1.3 mg (9% yield) of the title compound as an oil. LC-MS-TOF (m/z) 297 (MH+); tR=3.11, (UV, ELSD) 97%, 99%.

後処理

  1. concentrationThe reaction mixture was concentrated in vacuo, sodium hydroxide (2 M, 1.5 mL)
  2. additionwas added
  3. extractionthe product was extracted with isopropyl acetate (3×1.5 mL)
  4. dry with materialThe combined organic phases were dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. dissolutionredissolved in dimethyl sulfoxide (0.50 mL) of which 0.25 mL
  7. customwas subjected to preparative LC-MS purification

出典と根拠

ORDレコード
ord-38376b492771437e802f75f9daca9be5
出典データセット
uspto-grants-2009_10
特許番号
US07601870B2

関連ノート

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