Water → 8-(2-Chlorobenzyloxy)-2-methylimidazo[1,2-a]pyridine

HRID 4295

Reaction equation

HRID 4295 reaction equation
[H-].[Na+].[OH:3][C:4]1[C:5]2[N:6]([CH:10]=[C:11]([CH3:13])[N:12]=2)[CH:7]=[CH:8][CH:9]=1.[Cl:14][C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[CH2:17]Cl.O>CS(C)=O>[Cl:14][C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[CH2:17][O:3][C:4]1[C:5]2[N:6]([CH:10]=[C:11]([CH3:13])[N:12]=2)[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 119062-Chlorobenzyl chlorideHCID 24758Sodium hydrideHCID 8209532-Methylimidazo[1,2-a]pyridin-8-ol

Product 1

HCID 138259328-(2-Chlorobenzyloxy)-2-methylimidazo[1,2-a]pyridineYield 66.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A 60% dispersion of sodium hydride in mineral oil (1.87 g) was added portionwise to a suspension of 8-hydroxy-2-methylimidazo[1,2-a]pyridine (6.3 g) in dimethyl sulfoxide (63 ml) at room temperature over a period of 15 minutes. After being stirred for 30 minutes, 2-chlorobenzyl chloride (7.54 g) was added in one portion to the mixture and then the resultant mixture was stirred for 24 hours at room temperature. The mixture was poured into water and the resulting precipitate was collected by filtration. The crude product was purified by column chromatography on silica gel (30 g) with methylene chloride as an eluent to afford a solid, which was recrystallized from a mixture of diethyl ether and n-hexane to give 8-(2-chlorobenzyloxy)-2-methylimidazo[1,2-a]pyridine (7.75 g).

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. customThe crude product was purified by column chromatography on silica gel (30 g) with methylene chloride as an eluent
  3. customto afford a solid, which
  4. customwas recrystallized from a mixture of diethyl ether and n-hexane

Sources & evidence

ORD record
ord-d1e537d445bf410db0fd0a5741375d9f
Source dataset
uspto-grants-1988_02
Patent number
US04725601

Linked notes

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