Potassium Carbonate → HCID 69331779, compound

HRID 351257Notes

Reaction equation

HRID 351257 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:19]([C:20]3[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[N:24][CH:25]=3)[N:18]=[C:17]([OH:28])[CH:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:29](=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(=O)(OC)OC>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[N:19]([C:20]3[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[N:24][CH:25]=3)[N:18]=[C:17]([O:28][CH3:29])[CH:16]=2)=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 178492088HCID 178492088, compound

Product 1

HCID 69331779HCID 69331779, compoundYield 128.8%

Reagents, catalysts & solvents 2

HCID 12021Dimethyl CarbonateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A suspension of 5-{5-[4-(benzyloxy)phenyl]-3-hydroxy-1H-pyrazol-1-yl}-2-methoxypyridine (800 mg), dimethyl carbonate (0.9 mg) and potassium carbonate (888 mg) in DMF (8 ml) was stirred at 120° C. for 5 hours. The mixture was poured into ice water and extracted with AcOEt. The organic layer was washed with H2O, saturated aqueous sodium chloride solution, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by silica gel column chromatography eluted with AcOEt/n-hexane=30% to give 5-{5-[4-(benzyloxy)phenyl]-3-methoxy-1H-pyrazol-1-yl}-2-methoxy-pyridine (1.069 g) as a solid.

Workup

  1. extractionextracted with AcOEt
  2. washThe organic layer was washed with H2O, saturated aqueous sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography
  6. washeluted with AcOEt/n-hexane=30%

Sources & evidence

ORD record
ord-0ff61957493e4a43b77dfd22ec9972b3
Source dataset
uspto-grants-2007_02
Patent number
US07183306B2

Reaction notes

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