Potassium Carbonate → 8-(2,6-Dichloro-3-nitrobenzyloxy)-2-methylimidazo[1,2-a]pyridine

HRID 1899975Notes

Reaction equation

HRID 1899975 reaction equation
[OH:1][C:2]1[C:3]2[N:4]([CH:8]=[C:9]([CH3:11])[N:10]=2)[CH:5]=[CH:6][CH:7]=1.[Cl:12][C:13]1[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][CH:18]=[C:17]([Cl:24])[C:14]=1[CH2:15]Br.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[Cl:12][C:13]1[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][CH:18]=[C:17]([Cl:24])[C:14]=1[CH2:15][O:1][C:2]1[C:3]2[N:4]([CH:8]=[C:9]([CH3:11])[N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 8209532-Methylimidazo[1,2-a]pyridin-8-olHCID 110115352,6-Dichloro-3-nitrobenzyl Bromide

Product 1

HCID 108078918-(2,6-Dichloro-3-nitrobenzyloxy)-2-methylimidazo[1,2-a]pyridineYield 24.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 8-hydroxy-2-methylimidazo[1,2-a]pyridine (207 mg), 2,6-dichloro-3-nitrobenzyl bromide (400 mg) and potassium carbonate (580 mg) in N,N-dimethylformamide (8 ml) was stirred for 2 hours at 60° C. The mixture was cooled and diluted with water. The separated oil was extracted with dichloromethane. The organic layer was washed with water, dried, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel to give 8-(2,6-dichloro-3-nitrobenzyloxy)-2-methylimidazo[1,2-a]pyridine (120 mg) as crystals.

Workup

  1. temperatureThe mixture was cooled
  2. extractionThe separated oil was extracted with dichloromethane
  3. washThe organic layer was washed with water
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-b0c3501d80fa48bb925c88508267a90e
Source dataset
uspto-grants-1996_11
Patent number
US05574042

Reaction notes

Loading…