Tributylvinyltin → N-(4-Methyl-6-vinyl-pyridin-2-yl)-acetamide

HRID 2250403Notes

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]=1

Participants

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).

Workup

customThereafter, the volatile components are removed in vacuo
customthe remaining residue is purified by chromatography on silica gel (eluent: toluene/ethyl acetate 6:1)

Sources & evidence

ORD record: ord-d20669b33bd2432fa63b3144c4e3bd55
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07317021B2

Reaction notes

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