Potassium Phosphate, Tribasic → [4-(4-Methoxyphenyl)-8-(trifluoromethyl)quinolin-3-yl](phenyl)methanone

HRID 2104501Notes

Reaction equation

HRID 2104501 reaction equation
FC(F)(F)S(O[C:7]1[C:16]2[C:11](=[C:12]([C:17]([F:20])([F:19])[F:18])[CH:13]=[CH:14][CH:15]=2)[N:10]=[CH:9][C:8]=1[C:21](=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=O)=O.[CH3:31][O:32][C:33]1[CH:38]=[CH:37][C:36](B(O)O)=[CH:35][CH:34]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1>[CH3:31][O:32][C:33]1[CH:38]=[CH:37][C:36]([C:7]2[C:16]3[C:11](=[C:12]([C:17]([F:18])([F:19])[F:20])[CH:13]=[CH:14][CH:15]=3)[N:10]=[CH:9][C:8]=2[C:21]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:28])=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 201262(4-Methoxyphenyl)boronic acidHCID 160903243-Benzoyl-8-(trifluoromethyl)quinolin-4-yl trifluoromethanesulfonate

Product 1

HCID 11165686[4-(4-Methoxyphenyl)-8-(trifluoromethyl)quinolin-3-yl](phenyl)methanoneYield 81%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 3-benzoyl-8-(trifluoromethyl)quinolin-4-yl trifluoromethanesulfonate (1.8 g, 4 mmol), 4-methoxyphenylboronic acid(1.0 g, 6.5 mmol), and K3PO4(3.0 g) in dioxane (50 ml) was heated to reflux. After, 4 hr, the reaction was cooled, filtered, concentrated to give an oil which was purified by column chromatography (eluent 10% EtOAc/Hex) to give a white solid (1.3 g Yield=81%); MS (ESI) m/z 408 ([M+H]+;

Workup

  1. temperatureAfter, 4 hr, the reaction was cooled
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customto give an oil which
  5. customwas purified by column chromatography (eluent 10% EtOAc/Hex)
  6. customto give a white solid (1.3 g Yield=81%)

Sources & evidence

ORD record
ord-8648148d720047cfb6be4894ba6196a4
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

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