Tributylvinyltin → HCID 21931698, compound

HRID 1244047Notes

Reaction equation

HRID 1244047 reaction equation
Br[C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[C:4]([N+:10]([O-:12])=[O:11])[N:3]=1.[CH2:13]([Sn](CCCC)(CCCC)C=C)[CH2:14]CC>C1(C)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd](Cl)Cl>[CH3:9][O:8][C:7]1[C:2]([CH:13]=[CH2:14])=[N:3][C:4]([N+:10]([O-:12])=[O:11])=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 81998TributylvinyltinHCID 126928732-Bromo-3-methoxy-6-nitropyridine

Product 1

HCID 21931698HCID 21931698, compoundYield 81.3%

Reagents, catalysts & solvents 2

HCID 13169693Triphenylphosphine palladium dichlorideCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 1.0 g (4.3 mmol) 2-bromo-3-methoxy-6-nitropyridine (J. Lombardino, J. Med. Chem. 1981, 24, 39–42) in 25 ml of toluene was added 1.9 ml (6.4 mmol) of tri-n-butyl-vinyltin and a catalytic amount of bis(triphenylphosphine-palladium(II) chloride, and the reaction was refluxed under a nitrogen atmosphere for 2 hours. The reaction mixture was cooled to room temperature and the solvent evaporated. The residue was chromatographed on silica using chloroform as the elutant. Appropriate fractions were combined to yield 0.63 g of 3-methoxy-6-nitro-2-vinyl-pyridine as an oil. TLC: Rf=0.5 (5:1 hexane/ethyl acetate). 1H NMR (CDCl3) δ 8.15 (d, 1H), 7.35 (d, 1H), 7.10 (m, 1H), 6.55 (d, 1H), 5.65 (d, 1H), 4.0 (s, 3H). Mass spectrum: m/e=181.1 (p+1).

Workup

  1. customthe solvent evaporated
  2. customThe residue was chromatographed on silica

Sources & evidence

ORD record
ord-6639fb8563984899bfe9c826e41fefb1
Source dataset
uspto-grants-2006_10
Patent number
US07119207B2

Reaction notes

Loading…