Sodium hydride → [6-Chloro-5-(2-chloro-benzoyl)-pyrazin-2-yl]-(2-fluoro-phenyl)-acetic acid methyl ester

HRID 230164Notes

Reaction equation

HRID 230164 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]([C:12]1[C:17]([Cl:18])=[N:16][C:15](Cl)=[CH:14][N:13]=1)=[O:11].[CH3:20][O:21][C:22](=[O:31])[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[F:30]>CN(C=O)C>[CH3:20][O:21][C:22](=[O:31])[CH:23]([C:15]1[CH:14]=[N:13][C:12]([C:10](=[O:11])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[Cl:3])=[C:17]([Cl:18])[N:16]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[F:30]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2733230Methyl 2-fluorophenylacetateHCID 59812791(2-Chlorophenyl)-(3,5-dichloropyrazin-2-yl)methanone

Product 1

HCID 59834346[6-Chloro-5-(2-chloro-benzoyl)-pyrazin-2-yl]-(2-fluoro-phenyl)-acetic acid methyl esterYield 94.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of sodium hydride (0.175 g, 7 mmol) and (2-Chloro-phenyl)-(3,5-dichloro-pyrazin-2-yl)-methanone (0.86 g, 2.99 mmol) in 5 mL DMF was added (2-Fluoro-phenyl)-acetic acid methyl ester (0.503 g, 2.99 mmol). The reaction mixture was stirred for one hour at room temperature, and then was quenched by addition of water and aqueous HCl. The aqueous mixture was extracted with methylene chloride, and the combined organic phases were dried over MgSO4, filtered, and evaporated under reduced pressure to give 1.19 g of crude [6-Chloro-5-(2-chloro-benzoyl)-pyrazin-2-yl]-(2-fluoro-phenyl)-acetic acid methyl ester. Mass Spec. M+H=419.

Workup

  1. customwas quenched by addition of water and aqueous HCl
  2. extractionThe aqueous mixture was extracted with methylene chloride
  3. dry with materialthe combined organic phases were dried over MgSO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-9397369a694d406c9291a5ac6045c887
Source dataset
uspto-grants-2009_07
Patent number
US07566708B2

Reaction notes

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