Tributylamine → HCID 53889356, compound

HRID 1251919Notes

Reaction equation

HRID 1251919 reaction equation
C(N(CCCC)CCCC)CCC.FC(F)(F)S(O[C:20]1[C:21]([C:26]([O:28][CH3:29])=[O:27])=[N:22][CH:23]=[CH:24][CH:25]=1)(=O)=O.[F:32][C:33]1[CH:40]=[CH:39][C:36]([CH:37]=[CH2:38])=[CH:35][CH:34]=1>CN(C=O)C.[Cu]I>[F:32][C:33]1[CH:40]=[CH:39][C:36]([CH:37]=[CH:38][C:20]2[C:21]([C:26]([O:28][CH3:29])=[O:27])=[N:22][CH:23]=[CH:24][CH:25]=2)=[CH:35][CH:34]=1

Participants

6

Reactant 3

HCID 7622TributylamineHCID 678834-FluorostyreneHCID 11066008Methyl 3-(trifluoromethylsulfonyloxy)-pyridine-2-carboxylate

Product 1

HCID 53889356HCID 53889356, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Tributylamine (24.6 ml) was added to a stirred mixture of methyl 3-(trifluoromethanesulfonyloxy)pyridin-2-carboxylate (19.6 g), bis (triortho-tolylphosphine)palladium(II) chloride (1.08 g), copper (I) iodide (0.1 3 g) and 4-fluorostyrene (12.3 ml) in DMF (300 ml). The solution was heated under an inert atmosphere at 90° C. for 26 hours then cooled to ambient temperature and concentrated under reduced pressure. The residue was dissolved in dichloromethane (300 ml), the solid filtered and the filtrate washed with 1M. citric acid (3×100 ml), saturated aqueous sodium bicarbonate (150 ml), dried and concentrated under reduced pressure. The brown oil obtained was pre-absorbed onto silica then purified on a silica flash column eluting with ethyl acetate/iso-hexane (4:6) to give methyl 3-[2-(4-fluorophenyl)ethenyl]pyridin-2-carboxylate as a pale yellow solid (12.4 g).

Workup

  1. temperaturethen cooled to ambient temperature
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in dichloromethane (300 ml)
  4. filtrationthe solid filtered
  5. washthe filtrate washed with 1M
  6. dry with materialcitric acid (3×100 ml), saturated aqueous sodium bicarbonate (150 ml), dried
  7. concentrationconcentrated under reduced pressure
  8. customThe brown oil obtained
  9. customwas pre-absorbed onto silica
  10. customthen purified on a silica flash column
  11. washeluting with ethyl acetate/iso-hexane (4:6)

Sources & evidence

ORD record
ord-bf1d2095da4d44fdb86cda7c7fac107a
Source dataset
uspto-grants-2002_01
Patent number
US06342765B1

Reaction notes

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