Lithium Chloride → 2,2-Dimethyl-5-(6-methoxypyridin-2-yl)-4H-(1,3)benzodioxin-4-one

HRID 865916Notes

Reaction equation

HRID 865916 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.[CH3:22][O:23][C:24]1[N:29]=[C:28]([Sn](CCCC)(CCCC)CCCC)[CH:27]=[CH:26][CH:25]=1.[Cl-].[Li+]>O1CCOCC1.C(C1C=C(C)C=C(C(C)(C)C)C=1O)(C)(C)C>[CH3:1][C:2]1([CH3:21])[O:7][C:6]2[CH:8]=[CH:9][CH:10]=[C:11]([C:28]3[CH:27]=[CH:26][CH:25]=[C:24]([O:23][CH3:22])[N:29]=3)[C:5]=2[C:4](=[O:20])[O:3]1

Participants

6

Reactant 3

HCID 433294Lithium ChlorideHCID 105248912-Methoxy-6-(tributylstannyl)pyridineHCID 108927482,2-Dimethyl-4-oxo-4H-benzo[D][1,3]dioxin-5-YL trifluoromethanesulfonate

Product 1

HCID 152794162,2-Dimethyl-5-(6-methoxypyridin-2-yl)-4H-(1,3)benzodioxin-4-oneYield 95.5%

Reagents, catalysts & solvents 2

HCID 314042,6-Di-tert-butyl-4-methylphenolCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
140 °C

Procedure

10.9 g of 2,2-dimethyl-5-trifluoromethylsulfonyloxy-4H-(1,3)-benzodioxin-4-one, 16.0 g of 6-methoxy-2-tributylstannylpyridine, 4.25 g of lithium chloride, 0.78 g of tetrakistriphenylphosphinepalladium0 and 40 mg of 2,6-di-t-butyl-4-methylphenol are dissolved in 120 ml of dioxane and the mixture is stirred for 4 h at 140° C. in an autoclave. It is concentrated in vacuo and the product is chromatographed on silica gel 60 using ethyl acetate/toluene. 9.1 g (95%) of a solid of m.p. 130°-132° C. are obtained.

Workup

  1. concentrationIt is concentrated in vacuo
  2. customthe product is chromatographed on silica gel 60 using ethyl acetate/toluene

Sources & evidence

ORD record
ord-d4881b21e4ca44259d6a1451eace127a
Source dataset
uspto-grants-1996_10
Patent number
US05569640

Reaction notes

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