Ethyl bromoacetate → HCID 15896324, compound

HRID 566712Notes

Reaction equation

HRID 566712 reaction equation
[Na].[F:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:17])[CH2:10][C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=[CH:5][CH:4]=1.Br[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]>C(O)C>[F:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([CH:10]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[O:17])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 5360545Sodium2×HCID 103308811-(4-Fluorophenyl)-2-(pyridin-4-yl)ethan-1-one

Product 1

HCID 15896324HCID 15896324, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium (400 mg, 17.40 mmol) was added to a stirred solution of 1-(4-fluorophenyl)-2-(4-pyridyl)ethanone (3.35 g, 15.58 mmol) (P. J. Gilligan et al., J. Med. Chem. 35, 4344, 1992) in ethanol (50 ml) at room temperature. After dissolution of the sodium, ethyl bromoacetate (1.93 ml, 17.40 mmol) was added dropwise at ice-bath temperature. After stirring for 4 h at room temperature, the reaction mixture was concentrated by evaporation. It was diluted with dichloromethane and made neutral by washing with diluted acetic acid followed by drying of the organic solution and evaporation. Flash chromatography (hexane-acetone=3:1,2:1) provided the title compound as a syrup. MS (m/z): 302.2 (M+H)+; C17H16FNO3 requir. 301.3.

Workup

  1. additionwas added dropwise at ice-bath temperature
  2. concentrationthe reaction mixture was concentrated by evaporation
  3. additionIt was diluted with dichloromethane
  4. washby washing with diluted acetic acid
  5. customby drying of the organic solution and evaporation

Sources & evidence

ORD record
ord-159ba7c61a64446e9c36a9562ca2ea77
Source dataset
uspto-grants-2001_01
Patent number
US06174901B1

Reaction notes

Loading…