Potassium Fluoride → HCID 86641940, compound

HRID 384110Notes

Reaction equation

HRID 384110 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:4][N:3]=1.C([Sn](CCCC)(CCCC)/[CH:28]=[CH:29]/[C:30]([O:32][CH2:33][CH3:34])=[O:31])CCC.[F-].[K+]>CN(C)C=O.O>[O:16]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[CH2:9][O:8][C:5]1[CH:6]=[CH:7][C:2](/[CH:28]=[CH:29]/[C:30]([O:32][CH2:33][CH3:34])=[O:31])=[N:3][CH:4]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 522689Potassium FluorideHCID 10949132HCID 10949132, compoundHCID 86641939HCID 86641939, compound

Product 1

HCID 86641940HCID 86641940, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-bromo-5-((2-phenoxybenzyl)oxy)pyridine (1.0 g) in dimethylformamide (7 ml), 1.26 g of ethyl (2E)-3-(tributylstannyl)acrylate and 350 mg of tetrakis triphenylphosphine palladium were added, and the reaction solution was stirred overnight at 100° C. under nitrogen atmosphere. The reaction solution was cooled, then 15 ml of a saturated aqueous potassium fluoride solution was added, and the reaction solution was stirred for 1 hour, followed by removing insoluble matters by filtration through Celite and the filtrate was concentrated under reduced pressure. The residue obtained was diluted with water, extracted with diethyl ether, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue obtained was purified by silica gel column chromatography (eluent: ethyl acetate/hexane (0:100-25:75-30:70)) to afford the title compound as a yellow solid.

Workup

  1. temperatureThe reaction solution was cooled
  2. stirringthe reaction solution was stirred for 1 hour
  3. customby removing insoluble matters
  4. filtrationby filtration through Celite
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue obtained
  7. extractionextracted with diethyl ether
  8. dry with materialdried over magnesium sulfate
  9. distillationThe solvent was distilled off under reduced pressure
  10. customthe residue obtained
  11. customwas purified by silica gel column chromatography (eluent: ethyl acetate/hexane (0:100-25:75-30:70))

Sources & evidence

ORD record
ord-e75affcb75b54169ab0a899643dd84ce
Source dataset
uspto-grants-2013_02
Patent number
US08367708B2

Reaction notes

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