Stannane, tributyl(1-ethoxyethenyl)- → 8-(1-Ethoxyvinyl)-2-phenylquinoline

HRID 1056055Notes

Reaction equation

HRID 1056055 reaction equation
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH:8]=[CH:7]2.C([Sn](CCCC)(CCCC)[C:23]([O:25][CH2:26][CH3:27])=[CH2:24])CCC>C1(C)C=CC=CC=1.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>[CH2:26]([O:25][C:23]([C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH:8]=[CH:7]2)=[CH2:24])[CH3:27]

Participants

5

Reactant 2

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 707004958-Bromo-2-phenylquinoline

Product 1

HCID 897820818-(1-Ethoxyvinyl)-2-phenylquinoline

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

In a sealed tube, to the suspension of 8-bromo-2-phenylquinoline (0.1 g, 0.352 mmol) in toluene (5 mL) was added PdCl2(PPh3)2 (0.012 g, 0.017 mmol) and tributyl (1-ethoxyvinyl)stannane (0.15 g, 0.422 mmol) under N2. The reaction was heated at 80° C. for 12 h, then cooled to RT. The solvent was removed and the crude material was used in the next step without further purification.

Workup

  1. temperaturecooled to RT
  2. customThe solvent was removed
  3. customthe crude material was used in the next step without further purification

Sources & evidence

ORD record
ord-3b2faf61259145aea56ce4f3fa242058
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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