Stannane, tributyl(1-ethoxyethenyl)- → HCID 58119338, compound

HRID 1254074Notes

Reaction equation

HRID 1254074 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1.C([Sn](CCCC)(CCCC)[C:17]([O:19][CH2:20][CH3:21])=[CH2:18])CCC>O1CCOCC1.C(OCC)(=O)C.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>[CH2:20]([O:19][C:17]([C:2]1[CH:3]=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1)=[CH2:18])[CH3:21]

Participants

6

Reactant 2

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 7016458Methyl 5-bromopyridine-2-carboxylate

Product 1

HCID 58119338HCID 58119338, compoundYield 100.1%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of methyl 5-bromopyridine-2-carboxylate (5.0 g, 23.1 mg) in dioxane (80 ml) was added Pd(PPh3)4 (1.34 g, 1.16 mmol) and tributyl(1-ethoxyethenyl)stannane (8.60 ml, 25.5 mmol). After stirring the reaction mixture at reflux temp for overnight, the mixture was diluted with ethyl acetate, washed with 10% KF solution (aqueous), filtered though celite, dried, concentrated, and separated by HPLC (8-70% EtOH in hexane) to give methyl 5-(1-ethoxyethenyl)pyridine-2-carboxylate (4.8 g). LCMS: [M+H]+=208.2

Workup

  1. temperatureat reflux temp for overnight
  2. washwashed with 10% KF solution (aqueous)
  3. filtrationfiltered though celite
  4. customdried
  5. concentrationconcentrated
  6. customseparated by HPLC (8-70% EtOH in hexane)

Sources & evidence

ORD record
ord-31f61095f2de49de8d1867fbc1ba5d61
Source dataset
uspto-grants-2013_06
Patent number
US08455528B2

Reaction notes

Loading…