Potassium Carbonate → [4-(3-Methoxyphenyl)-8-(Trifluoromethyl)Quinolin-3-yl](Phenyl)Methanone

HRID 2104505Notes

Reaction equation

HRID 2104505 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[C:13]([C:18]([F:21])([F:20])[F:19])[CH:14]=[CH:15][CH:16]=3)[N:11]=[CH:10][C:9]=2[C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:23])[CH:5]=[CH:6][CH:7]=1.[C:30]([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH3:30][O:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[C:13]([C:18]([F:21])([F:19])[F:20])[CH:14]=[CH:15][CH:16]=3)[N:11]=[CH:10][C:9]=2[C:22]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[O:23])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 11773771[4-(3-Hydroxyphenyl)-8-(Trifluoromethyl)Quinolin-3-yl](Phenyl)Methanone2×

Product 1

HCID 11269781[4-(3-Methoxyphenyl)-8-(Trifluoromethyl)Quinolin-3-yl](Phenyl)MethanoneYield 48%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of [4-(3-hydroxyphenyl)-8-(trifluoromethyl)quinolin-3-yl](phenyl)methanone (0.20 g, 0.58 mmol), iodomethane (Example 42, 0.14 g, 1.0 mmol) and K2CO3 (0.41 g, 3 mmol) in acetone (10 ml) was heated to reflux. After 2 hr, the reaction was cooled, filtered, concentrated to give an oil which was purified by column chromatography (eluent 10% EtOAc/hexane) to give a the desired product as a foam (0.10 g, Yield=48%); MS (ESI) m/z 408 ([M+H]+)

Workup

  1. temperaturethe reaction was cooled
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customto give an oil which
  5. customwas purified by column chromatography (eluent 10% EtOAc/hexane)

Sources & evidence

ORD record
ord-b1ff4054957e466cac5576fec2d6861b
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

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