Methanol → HCID 178469439, compound

HRID 2363754Notes

Reaction equation

HRID 2363754 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[N:7]([CH:9]=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:11]=2)[CH:8]=1)#[CH:2].[N:17]([Si](C)(C)C)=[N+:18]=[N-:19].CN(C)C=O.CO>ClCCl>[NH:17]1[CH:2]=[C:1]([C:3]2[CH:4]=[CH:5][C:6]3[N:7]([CH:9]=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:11]=3)[CH:8]=2)[N:19]=[N:18]1

Participants

6

Reactant 4

HCID 887MethanolHCID 6228DimethylformamideHCID 78378AzidotrimethylsilaneHCID 44136342Ethyl 6-ethynylimidazo[1,2-a]pyridine-2-carboxylate

Product 1

HCID 178469439HCID 178469439, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 220 mg of ethyl 6-ethynylimidazo[1,2-a]pyridine-2-carboxylate and 0.21 mL of azidotrimethylsilane in 4 mL of a mixture (9/1) of N,N-dimethylformamide and methanol are added 9.8 mg of cuprous iodide. The reaction mixture is stirred for 2 hours at 100° C. and then cooled, diluted with 4 mL of dichloromethane, filtered through alumina and concentrated to dryness. The residue is chromatographed on silica, eluting with a mixture of dichloromethane and ethanol (97/3). The fractions containing the expected product are combined and concentrated to dryness under reduced pressure to give 125 mg of ethyl 6-(1H-1,2,3-triazol-4-yl)imidazo[1,2-a]pyridine-2-carboxylate in the form of an off-white solid.

Workup

  1. temperaturecooled
  2. filtrationfiltered through alumina
  3. concentrationconcentrated to dryness
  4. customThe residue is chromatographed on silica
  5. washeluting with a mixture of dichloromethane and ethanol (97/3)
  6. additionThe fractions containing the expected product
  7. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-1269da8990be4d8faf31e35639320f66
Source dataset
uspto-grants-2014_04
Patent number
US08691990B2

Reaction notes

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