5-Bromo-1-methylpyridin-2(1H)-one → HCID 68559883, compound

HRID 1481373Notes

Reaction equation

HRID 1481373 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.[CH2:10](C([Sn])=C(CCCC)CCCC)[CH2:11]CC>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:8][N:6]1[CH:7]=[C:2]([CH:10]=[CH2:11])[CH:3]=[CH:4][C:5]1=[O:9]

Participants

5

Reactant 2

HCID 130240275-Bromo-1-methylpyridin-2(1H)-oneHCID 53438229Tri(butyl)vinyltin

Product 1

HCID 68559883HCID 68559883, compoundYield 746.1%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

The title compound was prepared by following general procedure 2. To a solution of 5-bromo-1-methylpyridin-2(1H)-one (2 g, 10.63 mmol) in 20 mL of 1,4-dioxane, dichlorobis(triphenylphosphine)palladium(II) (0.834 g, 1.19 mmol) was added at RT and stirred at the same temperature for 5 min. Tributylvinyltin (3.46 mL, 1.19 mmol) was added slowly at RT and stirred at 100-105° C. for 2 h. The reaction was monitored by TLC and LCMS. After completion of the starting material, the solvent was evaporated and the residue purified by column chromatography using 60% ethyl acetate-hexane to afford 1.2 g of 1-methyl-5-vinylpyridin-2(1H)-one.

Workup

  1. customThe title compound was prepared
  2. stirringstirred at 100-105° C. for 2 h
  3. customAfter completion of the starting material, the solvent was evaporated
  4. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-2feb935625cc4347a61bde679f90dd80
Source dataset
uspto-grants-2016_08
Patent number
US09409910B2

Reaction notes

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