Sodium hydride → 3-[4-(4-chloro-2-cyano-1-pyrrolyl)benzyl]-2-ethylthio-7-methyl-3H-imidazo[4,5-b]pyridine

HRID 1707653Notes

Reaction equation

HRID 1707653 reaction equation
[CH2:1]([S:3][C:4]1[NH:13][C:7]2=[N:8][CH:9]=[CH:10][C:11]([CH3:12])=[C:6]2[N:5]=1)[CH3:2].[H-].[Na+].Br[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]2[CH:28]=[C:27]([Cl:29])[CH:26]=[C:25]2[C:30]#[N:31])=[CH:20][CH:19]=1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH2:1]([S:3][C:4]1[N:13]([CH2:17][C:18]2[CH:19]=[CH:20][C:21]([N:24]3[CH:28]=[C:27]([Cl:29])[CH:26]=[C:25]3[C:30]#[N:31])=[CH:22][CH:23]=2)[C:7]2=[N:8][CH:9]=[CH:10][C:11]([CH3:12])=[C:6]2[N:5]=1)[CH3:2]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 189619261-(4-Bromomethylphenyl)-4-chloropyrrole-2-carbonitrileHCID 178477331HCID 178477331, compound

Product 1

HCID 189619123-[4-(4-chloro-2-cyano-1-pyrrolyl)benzyl]-2-ethylthio-7-methyl-3H-imidazo[4,5-b]pyridineYield 28.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 2-ethylthio-7-methyl-3H-imidazo[4,5-b]pyridine (1.50 g) in dimethylformamide (15 ml) was added sodium hydride (341 mg) at room temperature under nitrogen atmosphere. The mixture was stirred for 30 minutes at the same room temperature under nitrogen atmosphere. To the mixture was added a solution of 1-(4-bromomethylphenyl)-4-chloropyrrole-2-carbonitrile (2.19 g) in dimethylformamide (15 ml). The mixture was stirred for 3 hours at room temperature. The mixture was treated with aqueous sodium bicarbonate solution, extracted twice with ethyl acetate. The extracts were washed with water, dried over magnesium sulfate, and evaporated. The residue was purified by silica gel column chromatography (eluted by n-hexane/ethyl acetate=1/1) to yield 2-ethylthio-3-[4-(4-chloro-2-cyano-1-pyrrolyl)benzyl]-7-methyl-3H-imidazo-[4,5-b]pyridine (850 mg) as a yellow oil.

Workup

  1. stirringThe mixture was stirred for 3 hours at room temperature
  2. extractionextracted twice with ethyl acetate
  3. washThe extracts were washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue was purified by silica gel column chromatography (eluted by n-hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-d69f510db59b45fe88c21374c473d6b7
Source dataset
uspto-grants-1994_10
Patent number
US05354759

Reaction notes

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