Sodium hydride → HCID 86757109, compound

HRID 1383442Notes

Reaction equation

HRID 1383442 reaction equation
[C:1]1([C:7]2[NH:8][CH:9]=[CH:10][N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].BrC[CH:16]1[CH2:20][CH:19]([CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]1>CN(C=O)C>[CH:19]1([CH:21]([C:4]2[CH:5]=[CH:6][C:1]([CH2:7][N:11]3[CH:10]=[CH:9][N:8]=[C:7]3[C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:2][CH:3]=2)[C:22]([O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:23])[CH2:18][CH2:17][CH2:16][CH2:20]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 695912-PhenylimidazoleHCID 18332380HCID 18332380, compound

Product 1

HCID 86757109HCID 86757109, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.44 g (10 mmol) of 2-phenylimidazole are dissolved in 10 ml of DMF, deprotonated (50° C.) using 330 mg (11 mmol) of NaH (80% strength) and the solution is then treated with 3.5 g (10 mmol) of tert-butyl 4-bromomethyl-2-cyclopentyl-acetate (DE 42 00 954 A1) and stirred overnight at RT. It is concentrated, the residue is dissolved in CH2Cl2, the solution is washed with H2O and concentrated and the residue is chromatographed on silica gel (cyclohexane/EA=8:2).

Workup

  1. custom(50° C.)
  2. concentrationIt is concentrated
  3. dissolutionthe residue is dissolved in CH2Cl2
  4. washthe solution is washed with H2O
  5. concentrationconcentrated
  6. customthe residue is chromatographed on silica gel (cyclohexane/EA=8:2)

Sources & evidence

ORD record
ord-0818b2105ee0497892c245a555b67ef6
Source dataset
uspto-grants-2001_07
Patent number
US06255330B1

Reaction notes

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