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

HRID 2207042Notes

Reaction equation

HRID 2207042 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-vinylquinoline

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. 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-68a71b456ad74446b3468ff3348639c6
Source dataset
uspto-grants-2016_06
Patent number
US09376392B2

Reaction notes

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