Water → HCID 4189037, compound

HRID 1626755Notes

Reaction equation

HRID 1626755 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7](B(O)O)[CH:8]=[CH:9][CH:10]=1)=[O:4].FC(F)(F)S(O[C:20]1[CH:21]=[CH:22][CH:23]=[C:24]2[C:29]=1[N:28]=[CH:27][CH:26]=[CH:25]2)(=O)=O.C(=O)([O-])[O-].[Na+].[Na+].O>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.CO.C1(C)C=CC=CC=1>[N:28]1[C:29]2[C:24](=[CH:23][CH:22]=[CH:21][C:20]=2[C:7]2[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=2)[C:3]([O:2][CH3:1])=[O:4])[CH:25]=[CH:26][CH:27]=1

Participants

8

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27347143-(Methoxycarbonyl)benzeneboronic acidHCID 36600898-Quinolinyl trifluoromethanesulfonate

Product 1

HCID 4189037HCID 4189037, compoundYield 86%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

1.04 g (5.77 mmol) of m-(methoxycarbonyl)phenyl boronic acid, 1.00 g (3.67 mmol) of quinolin-8-yl trifluoro-methanesulfonate, 125 mg (0.11 mmol) of tetrakis(triphenylphosphine)palladium(0), and 611 mg (5.77 mmol) of sodium carbonate were heated under reflux in a mixed solvent comprising 4 mL of H2O, 23 mL of toluene, and 6.7 mL of methanol for 20 hours. After the completion of the reaction, the organic solvent was distilled off under reduced pressure, H2O was added to the residue, and ethyl acetate extraction was performed. Subsequently, the organic layer was washed with saturated saline and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The obtained crude product was separated and purified by silica gel column chromatography, thereby giving 820 mg of methyl 3-(quinolin-8-yl)benzoate (yield: 86%).

Workup

  1. customAfter the completion of the reaction
  2. distillationthe organic solvent was distilled off under reduced pressure, H2O
  3. additionwas added to the residue, and ethyl acetate extraction
  4. washSubsequently, the organic layer was washed with saturated saline
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customThe obtained crude product
  8. customwas separated
  9. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-0fdb81257dc64c3aa235ca64c4c9d7d4
Source dataset
uspto-grants-2014_07
Patent number
US08785473B2

Reaction notes

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