Potassium Fluoride → HCID 12050204, compound

HRID 748523Notes

Reaction equation

HRID 748523 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.C([Sn](CCCC)(CCCC)[C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)CCC.[F-].[K+]>[Cl-].C([N+](CC)(CC)CC)C.C(#N)C.C(Cl)(Cl)Cl.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[N:19]1[CH:20]=[CH:21][CH:22]=[C:17]([C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][C:6](=[O:11])[CH2:5]3)[CH:18]=1

Participants

8

Reactant 3

HCID 522689Potassium FluorideHCID 6111935-Bromo-2-oxindoleHCID 34838483-(Tributylstannyl)pyridine

Product 1

HCID 12050204HCID 12050204, compoundYield 18%

Reagents, catalysts & solvents 4

HCID 5946Tetraethylammonium ChlorideCatalystHCID 13169693Triphenylphosphine palladium dichlorideCatalystHCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 5-bromooxindole (0.95 g, 4.48 mmol), 3-(tri-n-butylstannyl)pyridine (1.65 g, 4.48 mmol), tetraethyl ammonium chloride (2.23 g, 13.4 mmol) and bis(triphenylphospine palladium (II) chloride (0.16 g, 0.22 mmol) in acetonitrile (20 mL) was heated at reflux over night. After cooling to ambient temperature the mixture was diluted with chloroform (100 mL) and a potassium fluoride solution (10%, 250 mL) was added. The mixture was filtered through Celite and the layers were separated. The organic layer was dried (Na2SO4) and the solvent was removed in vacuo. The residue was purified on a silica gel column using chloroform/ethanol, (50:1), as the eluent affording 165 mg (18% yield) of the title compound as a white solid: 1H NMR (DMSO-d6, 400 MHz) δ 9.64 (br s, 1 H), 7.97 (d, J=2 Hz, 1 H), 7.66 (dd, J=5, 1 Hz, 1 H), 7.21-7.10 (m, 1 H), 6.73 (s, 1 H), 6.73-6.65 (m, 1 H), 6.65-6.54 (m, 1 H), 6.08 (d, J=8 Hz, 1 H), 2.69 (s, 2 H); MS (ES) m/z 211 (M++1).

Workup

  1. temperaturewas heated
  2. temperatureat reflux over night
  3. filtrationThe mixture was filtered through Celite
  4. customthe layers were separated
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. customthe solvent was removed in vacuo
  7. customThe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-e7c6dc38ff8e47eab91e37cfab54b8e4
Source dataset
uspto-grants-2008_07
Patent number
US07399780B2

Reaction notes

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