Tributylvinyltin → 5-Bromo-7-methyl-6-vinylquinoline

HRID 931746Notes

Reaction equation

HRID 931746 reaction equation
FC(F)(F)S(O[C:7]1[C:8]([Br:18])=[C:9]2[C:14](=[CH:15][C:16]=1[CH3:17])[N:13]=[CH:12][CH:11]=[CH:10]2)(=O)=O.[CH2:21]([Sn](CCCC)(CCCC)C=C)[CH2:22]CC.[Cl-].[Li+]>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Br:18][C:8]1[C:7]([CH:21]=[CH2:22])=[C:16]([CH3:17])[CH:15]=[C:14]2[C:9]=1[CH:10]=[CH:11][CH:12]=[N:13]2

Participants

6

Reactant 3

HCID 81998TributylvinyltinHCID 433294Lithium ChlorideHCID 866919795-Bromo-7-methylquinolin-6-yl trifluoromethanesulfonate

Product 1

HCID 666306625-Bromo-7-methyl-6-vinylquinolineYield 78%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-bromo-7-methylquinolin-6-yl trifluoromethanesulfonate (230 mg, 0.62 mmol), tributyl(vinyl)stannane (200 μL, 0.68 mmol), lithium chloride (78 mg, 1.86 mmol) and PdCl2(PPh3)2 (43 mg) in DMF (10 mL) was heated at 80° C. for 16 hours, and then the volatile component was removed in vacuo. The residue was dissolved in ethyl acetate (100 mL), washed with NaHCO3 solution, water and brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (hexanes/EtOAc) to provide 5-bromo-7-methyl-6-vinylquinoline (120 mg). LCMS-ESI+ (m/z): 248.2, 250.2 (M+H)+.

Workup

  1. customthe volatile component was removed in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate (100 mL)
  3. washwashed with NaHCO3 solution, water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (hexanes/EtOAc)

Sources & evidence

ORD record
ord-8703117344c54ace8062b9a4eca4b2be
Source dataset
uspto-grants-2016_03
Patent number
US09296758B2

Reaction notes

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