Sodium hydride → 2-(4-Fluorophenyl)-2-(3-nitropyridin-2-yl)-1-(pyridin-4-yl)ethanone

HRID 659944Notes

Reaction equation

HRID 659944 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=[O:10])=[CH:4][CH:3]=1.Cl[C:18]1[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][CH:21]=[CH:20][N:19]=1.[H-].[Na+].[Cl-].[NH4+]>CN(C)C=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:18]2[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][CH:21]=[CH:20][N:19]=2)[C:9]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=[O:10])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 796132-Chloro-3-nitropyridineHCID 110421332-(4-Fluorophenyl)-1-(pyridin-4-yl)ethanone

Product 1

HCID 117274532-(4-Fluorophenyl)-2-(3-nitropyridin-2-yl)-1-(pyridin-4-yl)ethanoneYield 79.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

21.5 g (100 mmoles) of 2-(4-fluorophenyl)-1-(pyridine-4-yl)ethanone (prepared as described in scheme 1) and 34.9 g of 2-chloro-3-nitropyridine are dissolved in 270 mL of dimethylformamide. 8.8 g of sodium hydride (60% in oil (220 mmoles) is slowly added to the reaction mixture which is kept between 0 and 5° C. After stirring for 1 hour at room temperature, the reaction mixture is poured into 1 L of ammonium chloride solution and extracted with ethyl acetate. The organic phase is washed with water and dried over magnesium sulfate. The oily residue is purified by chromatography on silica gel (ethylacetate/hexane 1/1) to give 26.7 g of 2-(4-Fluoro-phenyl)-2-(3-nitro-pyridin-2-yl)-1-pyridin-4-yl-ethanone.

Workup

  1. customis kept between 0 and 5° C
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with water
  4. dry with materialdried over magnesium sulfate
  5. customThe oily residue is purified by chromatography on silica gel (ethylacetate/hexane 1/1)

Sources & evidence

ORD record
ord-854a496b86ba490aa34ad31c0ddc02b9
Source dataset
uspto-grants-2011_12
Patent number
US08084395B2

Reaction notes

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