Sodium hydride → 3-Chloro-2-[4-(bis-[1,1-dimethylethoxycarbonyl]methyl)-3-nitrophenyl]-5-trifluoromethylpyridine

HRID 1276090Notes

Reaction equation

HRID 1276090 reaction equation
[H-].[Na+].[C:3]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])(=[O:12])[CH2:4][C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].[Cl:18][C:19]1[C:20]([C:29]2[CH:34]=[CH:33][C:32](F)=[C:31]([N+:36]([O-:38])=[O:37])[CH:30]=2)=[N:21][CH:22]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:24]=1>CN(C)C=O>[Cl:18][C:19]1[C:20]([C:29]2[CH:34]=[CH:33][C:32]([CH:4]([C:5]([O:7][C:8]([CH3:9])([CH3:10])[CH3:11])=[O:6])[C:3]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[C:31]([N+:36]([O-:38])=[O:37])[CH:30]=2)=[N:21][CH:22]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:24]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 68324Di-tert-butyl malonateHCID 221148423-Chloro-2-(4-fluoro-3-nitrophenyl)-5-(trifluoromethyl)pyridine

Product 1

HCID 221148383-Chloro-2-[4-(bis-[1,1-dimethylethoxycarbonyl]methyl)-3-nitrophenyl]-5-trifluoromethylpyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

0.9 g of an 80% strength by weight suspension of sodium hydride in mineral oil was added to 10 ml of anhydrous dimethylformamide. A solution of 5.1 g of di-tert-butyl malonate in 20 ml of dimethylformamide was added dropwise to this mixture, after which it was stirred for 30 minutes. A solution of 7.5 g of 3-chloro-2-(4-fluoro-3-nitrophenyl)-5-trifluoromethylpyridine in 20 ml of dimethylformamide was then added dropwise. The reaction mixture was stirred at 23° C. for 20 hours and at 80° C. for 5 hours. The cooled reaction mixture was then poured into 200 ml of ice water. The aqueous phase was extracted three times with 100 ml of tert-butyl methyl ether each time. The combined organic phases were washed with 100 ml of water, dried over sodium sulfate and concentrated. Yield: 10.8 g (79%) of a colorless oil.

Workup

  1. stirringThe reaction mixture was stirred at 23° C. for 20 hours and at 80° C. for 5 hours
  2. customThe cooled reaction mixture
  3. extractionThe aqueous phase was extracted three times with 100 ml of tert-butyl methyl ether each time
  4. washThe combined organic phases were washed with 100 ml of water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b8fdb020db1846deb6acc4ea3f56c35a
Source dataset
uspto-grants-2000_12
Patent number
US06165941

Reaction notes

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