Lithium Chloride → HCID 9882655, compound

HRID 374467Notes

Reaction equation

HRID 374467 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([Sn](C)(C)C)=[CH:5][N:4]=1.FC(F)(F)S(O[C:19]1[CH:20]=[N:21][C:22]2[C:27]([CH:28]=1)=[CH:26][C:25]([O:29][CH3:30])=[C:24]([O:31][CH3:32])[CH:23]=2)(=O)=O.[Cl-].[Li+]>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:19]2[CH:20]=[N:21][C:22]3[C:27]([CH:28]=2)=[CH:26][C:25]([O:29][CH3:30])=[C:24]([O:31][CH3:32])[CH:23]=3)=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 433294Lithium ChlorideHCID 10359684HCID 10359684, compoundHCID 150198012-Methoxy-5-(trimethylstannyl)pyridine

Product 1

HCID 9882655HCID 9882655, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 800 mg (2.94 mmol) of 2-methoxy-5-trimethylstannyl-pyridine, mg (2.94 mmol) of 6,7-dimethoxyquinolin-3-yl trifluoromethane sulfonate, 374 mg (8.82 mmol) of anhydrous lithium chloride and 170 mg (0.147 mmol) of Pd(PPh3)hd in 15 mL of anhydrous dioxane is flushed thoroughly with nitrogen and refluxed for 6 hours. The mixture is diluted with ethyl acetate (100 mL), washed with saturated NaHCO3 (75 mL), dried (Na2SO4) and evaporated. The resulting residue is chromatographed on silica gel (eluting with chloroform) to give a solid material which is recrystallized from ethyl acetate to give 3-(2-methoxypyrid-5-yl)-6,7-dimethoxyquinoline m.p. 170.5°-171.5° C.

Workup

  1. customis flushed thoroughly with nitrogen
  2. temperaturerefluxed for 6 hours
  3. additionThe mixture is diluted with ethyl acetate (100 mL)
  4. washwashed with saturated NaHCO3 (75 mL)
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customThe resulting residue is chromatographed on silica gel (eluting with chloroform)
  8. customto give a solid material which
  9. customis recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-3839602335864b7d96ca96471e1e635d
Source dataset
uspto-grants-1996_01
Patent number
US05480883

Reaction notes

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