Tributylvinyltin → 6-Vinylisoquinoline

HRID 598822Notes

Reaction equation

HRID 598822 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][CH:6]=[CH:5]2.[CH:12]([Sn](CCCC)(CCCC)CCCC)=[CH2:13]>O1CCOCC1.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>[CH:12]([C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][CH:6]=[CH:5]2)=[CH2:13]

Participants

5

Reactant 2

HCID 81998TributylvinyltinHCID 3136816-Bromoisoquinoline

Product 1

HCID 579507066-VinylisoquinolineYield 80.5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

In a 250 mL round bottom flask, 6-bromoisoquinoline (5 g, 24 mmol) (commercially available from Kalexsyn Product List Order Number 2003-005) was dissolved in dioxane (50 ml). Vinyltributylstannane (9 mL, 29 mmol) was added and the solution was degassed with nitrogen for 10 minutes. Tetrakis(triphenylphosphine)palladium (3 g, 2 mmol) was added in one portion. The reaction mixture was stirred for 3 hours at 100° C. The reaction mixture was adsorbed onto silica gel, and purified by flash chromatography (5-30%, EtOAc in hexane) to provide the product (3.0 g, 80%). LCMS (API-ES) m/z (%): 156 (M+H+).

Workup

  1. customthe solution was degassed with nitrogen for 10 minutes
  2. custompurified by flash chromatography (5-30%, EtOAc in hexane)

Sources & evidence

ORD record
ord-20f4cff5439f4a5eb74abe9a84d210cd
Source dataset
uspto-grants-2011_03
Patent number
US07897619B2

Reaction notes

Loading…