Tributylvinyltin → N-(4-Methyl-6-vinyl-pyridin-2-yl)-acetamide
Reaction equation
Br[C:2]1[N:7]=[C:6]([NH:8][C:9](=[O:11])[CH3:10])[CH:5]=[C:4]([CH3:12])[CH:3]=1.[CH:13]([Sn](CCCC)(CCCC)CCCC)=[CH2:14]>O1CCOCC1>[CH3:12][C:4]1[CH:3]=[C:2]([CH:13]=[CH2:14])[N:7]=[C:6]([NH:8][C:9](=[O:11])[CH3:10])[CH:5]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
37.5 g of N-(6-bromo-4-methyl-pyridin-2-yl)-acetamide (compound G4) is dissolved in 750 ml anoxic dioxane under a nitrogen atmosphere. Subsequently, 70.3 ml of vinyl tributylstannane and 11.5 g trans-dichloro-bis(triphenylphosphane)palladium-(II) are added. The reaction mixture is heated to 100° C. for 65 h. Thereafter, the volatile components are removed in vacuo and the remaining residue is purified by chromatography on silica gel (eluent: toluene/ethyl acetate 6:1) to afford 21.0 g of the title compound. M.p. 140° C. GC-MS: 176.2 (M+). TLC: Rf=0.40 (toluene/ethyl acetate 4:1).