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

HRID 986962Notes

Reaction equation

HRID 986962 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+]>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

5

Reactant 3

HCID 24758Sodium hydrideHCID 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 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(4-fluorophenyl)-1-(pyridin-4-yl)ethanone (4.0 g, 18.6 mmol) [prepared as described in Example 1 above] and 2-chloro-3-nitropyridine (6.50 g, 41.13 mmol) in dimethylformamide (50 ml) at 0° C. was added sodium hydride (1.65 g, 41 mmol, 60% in oil) under an argon atmosphere. The reaction mixture was warmed to room temperature and stirred for an hour. The reaction mixture was quenched with water and the product was extracted into ethyl acetate. The combined organic extracts were washed with brine, dried over MgSO4 and concentrated in vacuo to give a dark brown oil. Purification by flash column chromatography (10% to 50% ethyl acetate/hexanes gradient) gave 2-(4-fluorophenyl)-2-(3-nitropyridin-2-yl)-1-(pyridin-4-yl)ethanone as a brown oil (4.08 g).

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionthe product was extracted into ethyl acetate
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customto give a dark brown oil
  7. customPurification by flash column chromatography (10% to 50% ethyl acetate/hexanes gradient)

Sources & evidence

ORD record
ord-c467d23da16044db95968409f49d80d2
Source dataset
uspto-grants-2003_10
Patent number
US06630485B2

Reaction notes

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