Tributylvinyltin → 5-Bromo-2,7-dimethyl-6-vinylquinoline

HRID 2207050Notes

Reaction equation

HRID 2207050 reaction equation
FC(F)(F)S(O[C:7]1[C:8]([Br:19])=[C:9]2[C:14](=[CH:15][C:16]=1[CH3:17])[N:13]=[C:12]([CH3:18])[CH:11]=[CH:10]2)(=O)=O.[CH2:22]([Sn](CCCC)(CCCC)C=C)[CH2:23]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:19][C:8]1[C:7]([CH:22]=[CH2:23])=[C:16]([CH3:17])[CH:15]=[C:14]2[C:9]=1[CH:10]=[CH:11][C:12]([CH3:18])=[N:13]2

Participants

6

Reactant 3

HCID 81998TributylvinyltinHCID 433294Lithium ChlorideHCID 866919775-Bromo-2,7-dimethylquinolin-6-yl trifluoromethanesulfonate

Product 1

HCID 666313915-Bromo-2,7-dimethyl-6-vinylquinoline

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

PdCl2(PPh3)2 (207 mg, 0.30 mmol) was added to a solution of 5-bromo-2,7-dimethylquinolin-6-yl trifluoromethanesulfonate (1.13 g, 2.95 mmol), tributyl-vinyl-stannane (0.95 mL, 3.25 mmol), and lithium chloride (375 mg, 8.85 mmol) in DMF (30 mL). The reaction mixture was flushed with nitrogen, and heated at 80° C. for 4 hours. The mixture was diluted with ethyl acetate, washed with NaHCO3 solution, water and brine, and dried over Na2SO4. Concentration and purification by flash column chromatography yielded 5-bromo-2,7-dimethyl-6-vinylquinoline. LCMS-ESI+ (m/z): [M+H]+ calc'd for C13H13BrN: 262.0; Found: 262.1.

Workup

  1. customThe reaction mixture was flushed with nitrogen
  2. additionThe mixture was diluted with ethyl acetate
  3. washwashed with NaHCO3 solution, water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationConcentration and purification by flash column chromatography

Sources & evidence

ORD record
ord-aa6921a621ae4442b21dbcfef6cd9d38
Source dataset
uspto-grants-2016_06
Patent number
US09376392B2

Reaction notes

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