Dimethylformamide → HCID 15279439, compound

HRID 1955994Notes

Reaction equation

HRID 1955994 reaction equation
[CH3:1][C:2]1([CH3:21])[O:7][C:6]2[CH:8]=[CH:9][CH:10]=[C:11](OS(C(F)(F)F)(=O)=O)[C:5]=2[C:4](=[O:20])[O:3]1.C([Sn](CCCC)(CCCC)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=1)CCC.[Cl-].[Li+].CN(C)C=O>O1CCOCC1.O>[CH3:1][C:2]1([CH3:21])[O:7][C:6]2[CH:8]=[CH:9][CH:10]=[C:11]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=3)[C:5]=2[C:4](=[O:20])[O:3]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 433294Lithium ChlorideHCID 6077842-(Tributylstannyl)pyridineHCID 108927482,2-Dimethyl-4-oxo-4H-benzo[D][1,3]dioxin-5-YL trifluoromethanesulfonate

Product 1

HCID 15279439HCID 15279439, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

6.0 g (18.4 mmol) of 2,2-dimethyl-5-trifluoromethylsulfonyloxy-4H-(1,3)benzodioxin-4-one, 7.0 g (19.0 mmol) of 2-tributylstannylpyridine, 2.3 g (55.2 mmol) of lithium chloride and 420 mg (0.36 mmol) of tetrakistriphenylphosphinepalladium0 are dissolved in 60 ml of dioxane and 90 ml of dimethylformamide and the mixture is refluxed for 1.5 h (reaction temperature about 120° C.). It is stirred into 1.4 l of water at 0° C. and extracted with methyl tert-butyl ether, and the extract is washed with water and sodium chloride solution, dried over sodium sulfate and concentrated in vacuo. The residue is taken up in 60 ml of ethyl acetate, 8 g of potassium fluoride are added and the mixture is stirred overnight. The solid is filtered off and subsequently washed with plenty of ethyl acetate, and the filtrate is concentrated in vacuo. The crude product is purified by chromatography on silica gel 60 using hexane/ethyl acetate. Yield: 2.39 g (51%). Melting point: 142° C.

Workup

  1. custom(reaction temperature about 120° C.)
  2. extractionextracted with methyl tert-butyl ether
  3. washthe extract is washed with water and sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. addition8 g of potassium fluoride are added
  7. filtrationThe solid is filtered off
  8. washsubsequently washed with plenty of ethyl acetate
  9. concentrationthe filtrate is concentrated in vacuo
  10. customThe crude product is purified by chromatography on silica gel 60 using hexane/ethyl acetate

Sources & evidence

ORD record
ord-f54b7980d7a5452b931e2ba179a35a5f
Source dataset
uspto-grants-1998_07
Patent number
US05777118

Reaction notes

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