Potassium Carbonate → 3-(2-Butynyl)-4-chloro-3H-imidazo[4,5-c]pyridine

HRID 501436

Reaction equation

HRID 501436 reaction equation
[Cl:1][C:2]1[C:7]2[N:8]=[CH:9][NH:10][C:6]=2[CH:5]=[CH:4][N:3]=1.Br[CH2:12][C:13]#[C:14][CH3:15].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[CH2:12]([N:8]1[C:7]2[C:2]([Cl:1])=[N:3][CH:4]=[CH:5][C:6]=2[N:10]=[CH:9]1)[C:13]#[C:14][CH3:15]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27568621-Bromo-2-butyneHCID 53733644-Chloro-1H-imidazo[4,5-c]pyridine

Product 1

HCID 230707293-(2-Butynyl)-4-chloro-3H-imidazo[4,5-c]pyridine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.0 μg of 4-chloro-1H-imidazo[4,5-c]pyridine, 1.37 ml of 1-bromo-2-butyne, and 1.98 g of potassium carbonate were suspended in 15 ml of N,N-dimethylformamide, and the suspension was stirred at room temperature for 18 hours. The reaction solution was diluted with ethyl acetate, and washed with water. The organic layer was dried over anhydrous magnesium sulfate, then filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography. Thus, 1.79 g of a 1:1 mixture consisting of the title compound and the compound alkylated at the 1-position was obtained from the fraction eluted with hexane-ethyl acetate (1:2).

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography
  6. customwas obtained from the fraction
  7. washeluted with hexane-ethyl acetate (1:2)

Sources & evidence

ORD record
ord-4e79662faa7b4275ba4d474640fe3eaf
Source dataset
uspto-grants-2010_08
Patent number
US07772226B2

Linked notes

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