Tributylvinyltin → 2,2-Dimethyl-N-(5-vinylpyridin-2-yl)-propionamide

HRID 869873Notes

Reaction equation

HRID 869873 reaction equation
[CH2:1]([Sn](CCCC)(CCCC)C=C)[CH2:2]CC.Br[C:17]1[CH:18]=[CH:19][C:20]([NH:23][C:24](=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26])=[N:21][CH:22]=1>C1(C)C=CC=CC=1.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:1]([C:17]1[CH:18]=[CH:19][C:20]([NH:23][C:24](=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26])=[N:21][CH:22]=1)=[CH2:2]

Participants

5

Reactant 2

HCID 81998TributylvinyltinHCID 15461537N-(5-bromopyridin-2-yl)-2,2-dimethylpropanamide

Product 1

HCID 217020792,2-Dimethyl-N-(5-vinylpyridin-2-yl)-propionamideYield 80.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

Tributyl(vinyl)stannane (50 g, 0.16 mol), Pd(Ph3P)4 (3.3 g, 2.9 mmol) and a catalytic amount of 2,6-t-butyl-4-methylphenol was added to a solution of N-(5-bromopyridin-2-yl)pivalamide (36 g, 0.14 mol) in toluene. The reaction mixture was heated at reflux for 48 h. The solvent was evaporated in vacuo and the residue was purified by chromatography on silica gel (5% EtOAc in petroleum ether) to afford N-(5-vinylpyridin-2-yl)pivalamide (23 g, 80% yield). 1H NMR (CDCl3, 300 MHz) δ 8.24-8.20 (m, 2H), 8.02 (br s, 1H), 7.77 (dd, J=8.7 and 2.4, 1H), 6.65 (dd, J=17.7 and 10.8, 1H), 5.73 (d, J=17.7, 1H), 5.29 (d, J=10.8, 1H), 1.32 (s, 9H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 48 h
  3. customThe solvent was evaporated in vacuo
  4. customthe residue was purified by chromatography on silica gel (5% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-01ef9f7e80af43a89faf1f199d5532e8
Source dataset
uspto-grants-2015_03
Patent number
US08969386B2

Reaction notes

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