Water → HCID 21286349, compound

HRID 2231196Notes

Reaction equation

HRID 2231196 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.[N+:14]([C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Br)=[CH:19][CH:18]=1)([O-:16])=[O:15].O>CS(C)=O>[CH3:13][C:11]1[N:12]=[C:5]2[C:4]([O:3][CH2:21][C:20]3[CH:23]=[CH:24][C:17]([N+:14]([O-:16])=[O:15])=[CH:18][CH:19]=3)=[CH:9][CH:8]=[CH:7][N:6]2[CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 660114-Nitrobenzyl bromideHCID 8209532-Methylimidazo[1,2-a]pyridin-8-ol

Product 1

HCID 21286349HCID 21286349, compoundYield 40.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A 60% dispersion of sodium hydride in mineral oil (0.3 g) was added portionwise to a suspension of 8-hydroxy-2-methylimidazo[1,2-a]pyridine (1.0 g) in dimethyl sulfoxide (10 ml) at room temperature over a period of 15 minutes. After being stirred for 30 minutes, 4-nitrobenzyl bromide (1.6 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 ethyl acetate and n-hexane to give 2-methyl-8-(4-nitrobenzyloxy)imidazo[1,2-a]pyridine (0.77 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 ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-d0c135b2185549b2ae3444d2ceeb7a28
Source dataset
uspto-grants-1988_11
Patent number
US04782055

Reaction notes

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