Potassium Hydroxide → HCID 22112797, compound

HRID 564720Notes

Reaction equation

HRID 564720 reaction equation
Br[C:2]1[O:12][C:5]2=[C:6]([O:10][CH3:11])[N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=1.C(B(CC)[C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)C.[OH-].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[CH3:11][O:10][C:6]1[N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[C:2]([C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)[O:12][C:5]=12

Participants

7

Reactant 3

HCID 14797Potassium HydroxideHCID 6428513-(Diethylboryl)pyridineHCID 22112801HCID 22112801, compound

Product 1

HCID 22112797HCID 22112797, compoundYield 50.4%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2-Bromo-7-methoxyfuro[2,3-c]pyridine (0.6 g), diethyl(3-pyridyl)borane (0.387 g), tetrakis(triphenylphosphine)palladium(O) (0.157 g), potassium hydroxide (0.442 g) and tetrabutyl ammonium iodide (0.486 g) were combined in dry tetrahydrofuran (25 ml) under dry nitrogen. The mixture was heated to reflux for 1 hour. The solvent was removed in vacuo, and the residue partitioned between dichloromethane (20 ml) and water (20 ml). The aqueous layer was extracted with dichloromethane (20 ml). The combined organics were washed with water (24×40 ml), dried over magnesium sulfate, filtered and the solvent removed in vacuo. Purification by column chromatography on silica eluting with 2:1 heptane:ethyl acetate gave the title compound (0.30 g) as a white solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1 hour
  3. customThe solvent was removed in vacuo
  4. customthe residue partitioned between dichloromethane (20 ml) and water (20 ml)
  5. extractionThe aqueous layer was extracted with dichloromethane (20 ml)
  6. washThe combined organics were washed with water (24×40 ml)
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customthe solvent removed in vacuo
  10. customPurification by column chromatography on silica eluting with 2:1 heptane

Sources & evidence

ORD record
ord-8d7c0c025dfc4f988aa8c774c5b8ca39
Source dataset
uspto-grants-2001_01
Patent number
US06169090A

Reaction notes

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