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

HRID 1820145

Reaction equation

HRID 1820145 reaction equation
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

Participants

8

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 2734996copper(II) trifluoromethanesulfonateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

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%.

Workup

  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

Sources & evidence

ORD record
ord-38376b492771437e802f75f9daca9be5
Source dataset
uspto-grants-2009_10
Patent number
US07601870B2

Linked notes

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