1,4-Dioxane → HCID 11603785, compound

HRID 2242103Notes

Reaction equation

HRID 2242103 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1OS(C(F)(F)F)(=O)=O)=[CH:13][CH:12]=[C:11]([C:24]([F:27])([F:26])[F:25])[CH:10]=2)=[O:5])[CH3:2].P([O-])([O-])([O-])=O.[K+].[K+].[K+].O1[CH2:41][CH2:40][O:39][CH2:38]C1>C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[C:14]1[CH:15]=[C:6]([CH:4]=[O:3])[CH:7]=[CH:41][C:40]=1[O:39][CH3:38])=[CH:13][CH:12]=[C:11]([C:24]([F:27])([F:26])[F:25])[CH:10]=2)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 312751,4-DioxaneHCID 62657Potassium Phosphate, TribasicHCID 592051824-Trifluoromethanesulfonyloxy-7-trifluoromethyl-quinoline-3-carboxylic acid ethyl ester

Product 1

HCID 11603785HCID 11603785, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

4-Trifluoromethanesulfonyloxy-7-trifluoromethyl-quinoline-3-carboxylic acid ethyl ester (208 mg, 0.5 mmol), 5-formal-2-methoxylphenylboronic acid (100 mg, 0.55 mmol), tetrakis(triphenylphosphine)palladium(0) (29 mg) and potassium phosphate (159 mg, 0.75 mmol) were heated together in dioxane (5 mL) to 80° C. overnight. The reaction mixture was then diluted with ethyl acetate and washed with brine twice. The organic layer was dried over sodium sulfate, concentrated, and the residue purified by flash column eluted with 30% ethyl acetate in hexane to yield 4-(5-formyl-2-methoxy-phenyl)-7-trifluoromethyl-quinoline-3-carboxylic acid ethyl ester as a yellow solid.

Workup

  1. washwashed with brine twice
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated
  4. customthe residue purified by flash column
  5. washeluted with 30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-30c414afc08e46649aaa8ae2db80999a
Source dataset
uspto-grants-2010_03
Patent number
US07671065B2

Reaction notes

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