3-Bromopyridine → 3-(4-Methoxycarbonylbut-1-enyl)pyridine

HRID 326131Notes

Reaction equation

HRID 326131 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[C:8]([O:14][CH3:15])(=[O:13])[CH2:9][CH2:10][CH:11]=[CH2:12].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C(N(CC)CC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:15][O:14][C:8]([CH2:9][CH2:10][CH:11]=[CH:12][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1)=[O:13]

Participants

6

Reactant 3

HCID 122863-BromopyridineHCID 80271Tri-o-tolylphosphineHCID 543664Methyl 4-pentenoate

Product 1

HCID 537970273-(4-Methoxycarbonylbut-1-enyl)pyridine

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8471TriethylamineSolvent

Procedure

A solution of 3-bromopyridine (7.9 g), methyl 4-pentenoate (7.15 g), palladium acetate (0.11 g) and tri-o-tolylphosphine (0.6 g) in 50 ml of triethylamine is refluxed for 24 hours under argon and the solvent evaporated. The residue is taken up in methylene chloride (50 ml) and washed with water (2×40 ml). The organic phase is dried and evaporated to yield 3-(4-methoxycarbonylbut-1-enyl)pyridine as a colorless liquid; NMR (CDCl3) 3.72 (s, 3 H), 6.40 (s, 1 H); IR (film) 1725 cm-1.

Workup

  1. customthe solvent evaporated
  2. washwashed with water (2×40 ml)
  3. customThe organic phase is dried
  4. customevaporated

Sources & evidence

ORD record
ord-5d3f8e98d48c40df850c339eb5bb7a52
Source dataset
uspto-grants-1984_04
Patent number
US04444775

Reaction notes

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