Water → 2-Methyl-8-(3-methyl-4-pyridylmethoxy)-3-(2-propynyl)imidazo[1,2-a]pyridine

HRID 2231203Notes

Reaction equation

HRID 2231203 reaction equation
C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[C:9]2[N:10]([C:14]([CH2:18][C:19]#[CH:20])=[C:15]([CH3:17])[N:16]=2)[CH:11]=[CH:12][CH:13]=1.Cl[CH2:22][C:23]1[CH:28]=[CH:27][N:26]=[CH:25][C:24]=1[CH3:29].O>CN(C)C=O>[CH3:17][C:15]1[N:16]=[C:9]2[C:8]([O:7][CH2:22][C:23]3[CH:28]=[CH:27][N:26]=[CH:25][C:24]=3[CH3:29])=[CH:13][CH:12]=[CH:11][N:10]2[C:14]=1[CH2:18][C:19]#[CH:20]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 143683478-Hydroxy-2-methyl-3-(2-propynyl)imidazo[1,2-a]pyridineHCID 197578594-(Chloromethyl)-3-methylpyridine

Product 1

HCID 212863762-Methyl-8-(3-methyl-4-pyridylmethoxy)-3-(2-propynyl)imidazo[1,2-a]pyridineYield 74.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (0.52 g) was added to a solution of 8-hydroxy-2-methyl-3-(2-propynyl)imidazo[1,2-a]pyridine (0.5 g) and 4-chloromethyl-3-methylpyridine (0.53 g) in N,N-dimethylformamide (10 ml). The mixture was stirred under a nitrogen atmosphere for 5 hours at room temperature and then poured into water. The resulting precipitates were collected by filtration and recrystallized from ethyl acetate to give 2-methyl-8-(3-methyl-4-pyridylmethoxy)-3-(2-propynyl)imidazo[1,2-a]pyridine (0.58 g).

Workup

  1. customThe resulting precipitates
  2. filtrationwere collected by filtration
  3. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-fb7420b187a14658a3eaf5bda7a56bf1
Source dataset
uspto-grants-1988_11
Patent number
US04782055

Reaction notes

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