Water → 3-(4-bromo-2-chlorobenzyl)-2-methyl-3H-imidazo[4,5-b]pyridine-5-carbonitrile

HRID 1072796Notes

Reaction equation

HRID 1072796 reaction equation
[CH3:1][C:2]1[N:12]=[C:5]2[NH:6][C:7]([C:10]#[N:11])=[CH:8][CH:9]=[C:4]2[N:3]=1.[H-].[Na+].CS(O[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([Br:27])=[CH:23][C:22]=1[Cl:28])(=O)=O.O>CN(C)C=O>[Br:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][N:12]2[C:5]3=[N:6][C:7]([C:10]#[N:11])=[CH:8][CH:9]=[C:4]3[N:3]=[C:2]2[CH3:1])=[C:22]([Cl:28])[CH:23]=1.[Br:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][N:3]2[C:4]3[C:5](=[N:6][C:7]([C:10]#[N:11])=[CH:8][CH:9]=3)[N:12]=[C:2]2[CH3:1])=[C:22]([Cl:28])[CH:23]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 220586494-Bromo-2-chlorobenzyl methanesulfonateHCID 178432171HCID 178432171, compound

Product 2

HCID 223877943-(4-bromo-2-chlorobenzyl)-2-methyl-3H-imidazo[4,5-b]pyridine-5-carbonitrileHCID 223883031-(4-bromo-2-chlorobenzyl)-2-methyl-1H-imidazo[4,5-b]pyridine-5-carbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 2-methylimidazo[4,5-b]pyridine-5-carbonitrile (200 mg) in N,N-dimethylformamide (2 ml) was added sodium hydride (70% in mineral oil, 55 mg) under ice-cooling, and the mixture was stirred for 30 min. To this reaction mixture was added 4-bromo-2-chlorobenzyl methanesulfonate (450 mg), and the mixture was stirred for 2 hr at room temperature. The reaction mixture was poured into water and the product was extracted three times with ethyl acetate. The organic layers were combined and washed successively with water and saturated brine, dried over anhydrous magnesium sulfate and the solvent was evaporated. The residue was subjected to silica gel column chromatography (dichloromethane/ethyl acetate=5/1) to give two isomers, 3-(4-bromo-2-chlorobenzyl)-2-methyl-3H-imidazo[4,5-b]pyridine-5-carbonitrile (Rf 0.4, 233 mg) and 1-(4-bromo-2-chlorobenzyl)-2-methyl-1H-imidazo[4,5-b]pyridine-5-carbonitrile (Rf 0.1, 163 mg) as a white powder and a pale-yellow powder.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 2 hr at room temperature
  3. extractionthe product was extracted three times with ethyl acetate
  4. washwashed successively with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-ff5c8aa605fe4d0398e656b379de8c95
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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