Sodium hydride → HCID 19759390, compound

HRID 248389Notes

Reaction equation

HRID 248389 reaction equation
[C:1]([NH:6][C:7]1[C:12]([N+:13]([O-:15])=[O:14])=[C:11]([CH3:16])[CH:10]=[C:9]([CH3:17])[N:8]=1)(=[O:5])[CH2:2][CH2:3][CH3:4].[H-].[Na+].CS(O[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([N:32]2[C:36]([CH3:37])=[CH:35][CH:34]=[C:33]2[C:38]#[N:39])=[CH:28][CH:27]=1)(=O)=O>CN(C)C=O>[C:1]([N:6]([C:7]1[C:12]([N+:13]([O-:15])=[O:14])=[C:11]([CH3:16])[CH:10]=[C:9]([CH3:17])[N:8]=1)[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([N:32]2[C:36]([CH3:37])=[CH:35][CH:34]=[C:33]2[C:38]#[N:39])=[CH:28][CH:27]=1)(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 19759356HCID 19759356, compoundHCID 21464300HCID 21464300, compound

Product 1

HCID 19759390HCID 19759390, compoundYield 60.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 2-butyrylamino-4,6-dimethyl-3-nitropyridine (2.49 g) in dimethylformamide (12.5 ml) was added sodium hydride (441 mg) in an ice-water bath. The mixture was stirred at room temperature for an hour, and a solution of 1-(4-methanesulfonyloxymethylphenyl)-5-methylpyrrole-2-carbonitrile (3.05 g) in dimethylformamide (15 ml) was dropwise therein. The reaction mixture was stirred at room temperature for 5.5 hours and was stood overnight. The separated oil was extracted with ethyl acetate. The extract were washed with brine, dried, and concentrated in vacuo. The residue was purified by flash column chromatography eluted by n-hexane/ethyl acetate (1/1) to give 2-[N-butyryl-N-[4-(2-cyano-5-methyl-1-pyrrolyl)benzyl]amino]-4,6-dimethyl-3-nitropyridine (2.75 g) as oil.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 5.5 hours
  2. extractionThe separated oil was extracted with ethyl acetate
  3. washThe extract were washed with brine
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography
  7. washeluted by n-hexane/ethyl acetate (1/1)

Sources & evidence

ORD record
ord-dd649690d852469e92c026c1004cb683
Source dataset
uspto-grants-1993_05
Patent number
US05210092

Reaction notes

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