Tributylvinyltin → HCID 59822492, compound

HRID 1625974Notes

Reaction equation

HRID 1625974 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2[Cl:12].[CH2:13]([Sn](CCCC)(CCCC)C=C)[CH2:14]CC>O1CCOCC1>[Cl:12][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([CH:13]=[CH2:14])[CH:3]=2)[N:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 81998TributylvinyltinHCID 51395376-Bromo-4-chloroquinoline

Product 1

HCID 59822492HCID 59822492, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 6-bromo-4-chloroquinoline (6.52 g, 26.88 mmol; see J. Med. Chem., 21, 268 (1978)), tributyl(vinyl)tin (8.95 g, 28.22 mmol), and tetrakistriphenylphosphine palladium (0) (0.62 g, 0.54 mmol) in 1,4-dioxane (150 mL) was refluxed for 2.0 h, cooled to room temperature, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (0-4% MeOH:CH2Cl2) to give the title compound (5.1 g) as a pale yellow solid. MS(ES)+ m/e 190 [M+H]+. This material was used directly in the next step.

Workup

  1. temperaturewas refluxed for 2.0 h
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by flash chromatography on silica gel (0-4% MeOH:CH2Cl2)

Sources & evidence

ORD record
ord-7e98c81882604217a478acce69fc31a9
Source dataset
uspto-grants-2014_07
Patent number
US08785433B2

Reaction notes

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