Tributylvinyltin → 5,7-Difluoro-6-vinyl-quinoline

HRID 69138Notes

Reaction equation

HRID 69138 reaction equation
Br[C:2]1[C:3]([F:13])=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[N:8]=[CH:7][CH:6]=[CH:5]2.[CH2:14]([Sn](CCCC)(CCCC)C=C)[CH2:15]CC>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O1CCOCC1>[F:13][C:3]1[C:2]([CH:14]=[CH2:15])=[C:11]([F:12])[CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[N:8]2

Participants

5

Reactant 2

HCID 81998TributylvinyltinHCID 451083546-Bromo-5,7-difluoroquinoline

Product 1

HCID 579173805,7-Difluoro-6-vinyl-quinoline

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

6-Bromo-5,7-difluoro-quinoline (v) (1 g, 4.10 mmol), tetrakis(triphenylphosphine)palladium(0) (47 mg, 0.041 mmol) and tributyl(vinyl)tin (1.34 g, 4.10 mmol) were put together with dioxane (3.7 mL) in a microwave reactor and stirred for 25 min at 150° C. under microwave irradiations. The solvent was removed and the residue was purified by MPLC with hexane and EtOAc. The title compound was obtained as a colorless oil (tR 1.1 min (conditions 2), MH+=192).

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by MPLC with hexane and EtOAc

Sources & evidence

ORD record
ord-5956399fc5d24bb6874c2cc714505cd7
Source dataset
uspto-grants-2014_09
Patent number
US08822468B2

Reaction notes

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