Potassium Carbonate → HCID 57756374, compound

HRID 229058Notes

Reaction equation

HRID 229058 reaction equation
C(=O)([O-])[O-].[K+].[K+].I[C:8]1[C:13]([O:14][C:15]2[C:24]3[C:19](=[CH:20][C:21]([O:27][CH3:28])=[C:22]([O:25][CH3:26])[CH:23]=3)[N:18]=[CH:17][CH:16]=2)=[CH:12][CH:11]=[C:10]([CH3:29])[N:9]=1.CC1(C)C(C)(C)OC(B[C:39]2[CH:40]=[N:41][NH:42][CH:43]=2)O1>CN(C)C=O>[CH3:26][O:25][C:22]1[CH:23]=[C:24]2[C:19](=[CH:20][C:21]=1[O:27][CH3:28])[N:18]=[CH:17][CH:16]=[C:15]2[O:14][C:13]1[C:8]([C:39]2[CH:40]=[N:41][NH:42][CH:43]=2)=[N:9][C:10]([CH3:29])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 100936734-[(2-Iodo-6-methyl-3-pyridyl)oxy]-6,7-dimethoxyquinoline2×HCID 178431303HCID 178431303, compound

Product 1

HCID 57756374HCID 57756374, compoundYield 44.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

N,N-Dimethylformamide (1.2 ml) and a 2 M aqueous potassium carbonate solution (1 ml) were added to 4-[(2-iodo-6-methyl-3-pyridyl)oxy]-6,7-dimethoxy-quinoline (compound 116) (50 mg), tetrakistriphenylphosphine palladium (70 mg), and 4-(4,4,5,5-tetramethyl-[1,3]dioxolan-2-ylboranyl)-1H-pyrazole (34 mg) under an argon atmosphere, and the mixture was stirred at 70° C. for 4 hr. The reaction solution was cooled to room temperature and was then filtered through Celite. The solvent was removed from the filtrate by distillation under the reduced pressure. Water was added to the residue, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with water. The ethyl acetate layer was extracted with 1 N hydrochloric acid. The aqueous layer was then made alkaline by the addition of a 1 N aqueous sodium hydroxide solution and was extracted with ethyl acetate. The ethyl acetate layer was washed with water and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using hexane-acetone to give the title compound (19 mg, yield 44%).

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. filtrationwas then filtered through Celite
  3. customThe solvent was removed from the filtrate by distillation under the reduced pressure
  4. additionWater was added to the residue
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe ethyl acetate layer was then washed with water
  7. extractionThe ethyl acetate layer was extracted with 1 N hydrochloric acid
  8. additionby the addition of a 1 N aqueous sodium hydroxide solution
  9. extractionwas extracted with ethyl acetate
  10. washThe ethyl acetate layer was washed with water
  11. dry with materialwas dried over anhydrous sodium sulfate
  12. customThe solvent was removed by distillation under the reduced pressure
  13. customthe residue was purified by thin layer chromatography

Sources & evidence

ORD record
ord-079282a931954dc898c3295c4aae5561
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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