Ethylene → N-(5-Ethenyl-2-pyridinyl)-2-methylpropanamide

HRID 2051502Notes

Reaction equation

HRID 2051502 reaction equation
[C:1]([NH:6][C:7]1[CH:12]=[CH:11][C:10](Br)=[CH:9][N:8]=1)(=[O:5])[CH:2]([CH3:4])[CH3:3].[C:14]1(C)C=CC=C[C:15]=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C.C=C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(#N)C>[C:1]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([CH:14]=[CH2:15])=[CH:9][N:8]=1)(=[O:5])[CH:2]([CH3:4])[CH3:3]

Participants

7

Reactant 4

HCID 6325EthyleneHCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 14988412N-(5-Bromopyridin-2-yl)-2-methylpropanamide

Product 1

HCID 14988413N-(5-Ethenyl-2-pyridinyl)-2-methylpropanamide

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 9.72 g of 2 isobutyramido-5-bromopyridine, 0.49 g of tris-(0-tolyl)phosphine, 110 mg of palladium acetate, 10 ml of triethylamine and 30 ml of acetonitrile was heated at 80° C. in a glass lined vessel at 200 psi of ethylene for 18 hours. The reaction mixture was concentrated under reduced pressure and the residue chromatographed on el (0-25% ethyl acetate/methylene chloride) to give 6.67 g of pure product, m.p. 77°-8° C.; Analysis: Calc'd for C11H14N2O:

Workup

  1. customfor 18 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue chromatographed on el (0-25% ethyl acetate/methylene chloride)

Sources & evidence

ORD record
ord-6eb145df74e94ec7bcab48a258845391
Source dataset
uspto-grants-1991_05
Patent number
US05019578

Reaction notes

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