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

HRID 1442765
Notes
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Reaction equation

HRID 1442765 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 1140Toluene
Solvent

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, 9 H).

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-1cc595f2d746453897ce942a1a7d0b2e
Source dataset
uspto-grants-2010_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07659268B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes