2-Bromopropane → 5,7-dichloro-3-isopropyl-3H-imidazo[4,5-b]pyridine

HRID 2096992Notes

Reaction equation

HRID 2096992 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[N:8]=[CH:9][NH:10][C:5]2=[C:4]([Cl:11])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH:19]([CH3:21])[CH3:20]>CS(C)=O>[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([CH:19]([CH3:21])[CH3:20])[CH:9]=[N:10][C:5]2=[C:4]([Cl:11])[CH:3]=1

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 59498025,7-dichloro-1H-imidazo[4,5-b]pyridine

Product 1

HCID 866434695,7-dichloro-3-isopropyl-3H-imidazo[4,5-b]pyridineYield 57%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
18 °C

Procedure

A stirred solution of 5,7-Dichloroimidazo[4,5-b]pyridine (5 g, 26.5 mmol.) in DMSO (50 mL) was cooled in an ice bath, and treated with K2CO3 (14.6 g, 106.2 mmol.) and 2-bromopropane (12.47 mL, 132.8 mmol.). The mixture was allowed to warm to 18° C. and stirred overnight. The DMSO was removed in vacuo. A mixture of the residue and water (100 mL) was extracted with AcOEt (3×300 mL). The extractions were combined, washed with brine (300 mL), dried over (Na2SO4) and concentrated. Chromatography of the residue on silica gel with toluene-AcOEt-CH2Cl2 3:1:1 gave 5,7-Dichloro-3-iso-propylimidazo[4,5-b]pyridine. (Yield: 57%).

Workup

  1. customThe DMSO was removed in vacuo
  2. additionA mixture of the residue and water (100 mL)
  3. extractionwas extracted with AcOEt (3×300 mL)
  4. extractionThe extractions
  5. washwashed with brine (300 mL)
  6. dry with materialdried over (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-9a45a0c48e3741458cc989184e0eda13
Source dataset
uspto-grants-2013_05
Patent number
US08450342B2

Reaction notes

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