Sodium hydride → 2-[N-butyryl-N-[4-(4-chloro-2-cyano-1-pyrrolyl)benzyl]amino]-4-methyl-3-nitropyridine

HRID 248372Notes

Reaction equation

HRID 248372 reaction equation
[H-].[Na+].[C:3]([NH:8][C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[C:13]([CH3:18])[CH:12]=[CH:11][N:10]=1)(=[O:7])[CH2:4][CH2:5][CH3:6].Br[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]2[CH:31]=[C:30]([Cl:32])[CH:29]=[C:28]2[C:33]#[N:34])=[CH:23][CH:22]=1>CS(C)=O>[C:3]([N:8]([C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[C:13]([CH3:18])[CH:12]=[CH:11][N:10]=1)[CH2:20][C:21]1[CH:22]=[CH:23][C:24]([N:27]2[CH:31]=[C:30]([Cl:32])[CH:29]=[C:28]2[C:33]#[N:34])=[CH:25][CH:26]=1)(=[O:7])[CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 189619261-(4-Bromomethylphenyl)-4-chloropyrrole-2-carbonitrileHCID 214642392-Butyrylamino-4-methyl-3-nitropyridine

Product 1

HCID 197595662-[N-butyryl-N-[4-(4-chloro-2-cyano-1-pyrrolyl)benzyl]amino]-4-methyl-3-nitropyridine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent3×

Procedure

To a suspension of sodium hydride (114 mg, 60% oil dispersion) in dimethyl sulfoxide (5 ml) was added dropwise a solution of 2-butyrylamino-4-methyl-3-nitropyridine (605 mg) in dimethyl sulfoxide (10 ml) at ambient temperature under nitrogen atmosphere. The mixture was stirred at the same temperature for one hour and a solution of 1-(4-bromomethylphenyl)-4-chloropyrrole-2-carbonitrile (800 ml) in dimethyl sulfoxide (10 ml) was added therein. The reaction mixture was stirred at ambient temperature for 2 hours and quenched with ice water. The separated oil was extracted twice with ethyl acetate. The combined extracts were washed with water, dried, and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluted by n-hexane/ethylacetate (2/1-1/1) to yield 2-[N-butyryl-N-[4-(4-chloro-2-cyano-1-pyrrolyl)benzyl]amino]-4-methyl-3-nitropyridine (723 mg).

Workup

  1. stirringThe reaction mixture was stirred at ambient temperature for 2 hours
  2. customquenched with ice water
  3. extractionThe separated oil was extracted twice with ethyl acetate
  4. washThe combined extracts were washed with water
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography on silica gel
  8. washeluted by n-hexane/ethylacetate (2/1-1/1)

Sources & evidence

ORD record
ord-3bca4c37b7a34ab79886e7008dd9a727
Source dataset
uspto-grants-1993_05
Patent number
US05210092

Reaction notes

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