Potassium Carbonate → HCID 68652930, compound

HRID 1993767Notes

Reaction equation

HRID 1993767 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]2[C:9]([C:13]3[CH:18]=[CH:17][C:16]([N:19]4[CH:23]=[CH:22][CH:21]=[N:20]4)=[CH:15][C:14]=3[O:24][CH3:25])=[N:10][N:11]([CH3:12])[C:3]=12.C(=O)([O-])[O-].[K+].[K+]>O>[C:13]1([CH:9]=[CH:4][C:2]2[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]3[C:9]([C:13]4[CH:18]=[CH:17][C:16]([N:19]5[CH:23]=[CH:22][CH:21]=[N:20]5)=[CH:15][C:14]=4[O:24][CH3:25])=[N:10][N:11]([CH3:12])[C:3]=23)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 59134867HCID 59134867, compound2×

Product 1

HCID 68652930HCID 68652930, compoundYield 167.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Compound 5a (0.75 mL of the nominally 1.0 M solution, 0.75 mmol) was added via syringe to 7-chloro-3-[2-methoxy-4-(pyrazol-1-yl)phenyl]-1,5-dimethyl pyrazolo[4,3-b]pyridine (compound 4b, 200 mg, 0.57 mmol) under nitrogen and the mixture was evaporated to dryness. Dioxane (2 mL) and water (2 mL) were added, followed by potassium carbonate (157 mg, 1.14 mmol) and tetrakis (triphenylphosphine)palladium(0) (66 mg, 0.057 mmol). The mixture was stirred and heated to reflux for 6 hr and then was allowed to cool. Water (5 mL) was added and the mixture was extracted with ethyl acetate. The combined organic extracts were dried over sodium sulfate, concentrated, and the residue was chromatographed on silica gel using 1:2 hexanes/ethyl acetate to afford 7-(2-phenyl-1-ethenyl)-3-[2-methoxy-4-(pyrazol-1-yl)phenyl]-1,5-dimethylpyrazolo[4,3-b]pyridine (compound 5b, 201 mg) as a yellow oil.

Workup

  1. customthe mixture was evaporated to dryness
  2. additionDioxane (2 mL) and water (2 mL) were added
  3. temperatureheated
  4. temperatureto reflux for 6 hr
  5. temperatureto cool
  6. extractionthe mixture was extracted with ethyl acetate
  7. dry with materialThe combined organic extracts were dried over sodium sulfate
  8. concentrationconcentrated
  9. customthe residue was chromatographed on silica gel using 1:2 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-0563b20e42704ac88a90b0800cac0ae6
Source dataset
uspto-grants-2010_01
Patent number
US07652035B2

Reaction notes

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