Sodium hydride → HCID 19759303, compound

HRID 248367Notes

Reaction equation

HRID 248367 reaction equation
[CH2:1]([C:5]1[NH:14][C:8]2=[N:9][CH:10]=[CH:11][C:12]([CH3:13])=[C:7]2[N:6]=1)[CH2:2][CH2:3][CH3:4].[H-].[Na+].Br[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH:29]=[C:28]([Cl:30])[C:27]([Cl:31])=[C:26]2[C:32]#[N:33])=[CH:21][CH:20]=1>CS(C)=O>[CH2:1]([C:5]1[N:14]([CH2:18][C:19]2[CH:20]=[CH:21][C:22]([N:25]3[CH:29]=[C:28]([Cl:30])[C:27]([Cl:31])=[C:26]3[C:32]#[N:33])=[CH:23][CH:24]=2)[C:8]2=[N:9][CH:10]=[CH:11][C:12]([CH3:13])=[C:7]2[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 19759379HCID 19759379, compoundHCID 178441492HCID 178441492, compound

Product 1

HCID 19759303HCID 19759303, compoundYield 41.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a solution of 2-butyl-7-methyl-3H-imidazo[4,5-b]-pyridine (568 mg) in dimethyl sulfoxide (7 ml) was added sodium hydride (132 mg, 60% oil dispersion) at ambient temperature. The mixture was stirred for 40 minutes at the same temperature. To the mixture was added dropwise a solution of 1-(4-bromomethylphenyl)-3,4-dichloropyrrole-2-carbonitrile (990 mg) in dimethyl sulfoxide (3 ml). The mixture was stirred for 2 hours at ambient temperature and ice water (30 ml) was added therein. The separated oil was extracted twice with ethyl acetate. The extracts were washed with water, dried, and evaporated under reduced pressure. The residue was purified by silica gel column chromatography eluted by 50% ethyl acetate in n-hexane to give 2-butyl-3-[4-(2-cyano-3,4-dichloro-1-pyrrolyl)benzyl]-7-methyl-3H-imidazo[4,5-b]pyridine (546 mg) as an oil.

Workup

  1. stirringThe mixture was stirred for 2 hours at ambient temperature
  2. extractionThe separated oil was extracted twice with ethyl acetate
  3. washThe extracts were washed with water
  4. customdried
  5. customevaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography
  7. washeluted by 50% ethyl acetate in n-hexane

Sources & evidence

ORD record
ord-f6658f4ff4954b8bb31273dabe2e12a2
Source dataset
uspto-grants-1993_05
Patent number
US05210092

Reaction notes

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