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

HRID 1290158Notes

Reaction equation

HRID 1290158 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-fb7a12163a7d4033a992af19a7e91aef
Source dataset
uspto-grants-1998_05
Patent number
US05750699

Reaction notes

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