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

HRID 2207030
Notes
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Reaction equation

HRID 2207030 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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, compoundCatalyst
HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
80 °C

Procedure

PdCl2(PPh3)2 (207 mg, 0.30 mmol) were added to a mixture 5-bromo-2,7-dimethylquinolin-6-yl trifluoromethanesulfonate (1.13 g, 2.95 mmol), tributyl-vinyl-stannane (0.95 mL, 3.25 mmol), lithium chloride (375 mg, 8.85 mmol) in DMF (30 mL). The reaction mixture was flushed with nitrogen, heated at 80° C. for 4 hours, cooled to room temperature. The mixture was diluted by ethyl acetate, washed with NaHCO3 solution, water and brine, dried over Na2SO4, filtered and concentrated in vacuo. The obtained residue was purified by flash chromatography to provide the desired product. LCMS-ESI+: calc'd for C13H12BrN: 262.0 (M+H+); Found: 262.1 (M+H+).

Workup

  1. customThe reaction mixture was flushed with nitrogen
  2. temperaturecooled to room temperature
  3. additionThe mixture was diluted by ethyl acetate
  4. washwashed with NaHCO3 solution, water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe obtained residue was purified by flash chromatography

Sources & evidence

ORD record
ord-4ee15febd3ec48f5aeaec4c0a4e4d97d
Source dataset
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09376392B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes