Potassium Carbonate → HCID 11261037, compound

HRID 2104506Notes

Reaction equation

HRID 2104506 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.Br[CH2:31][C:32]1[CH:41]=[CH:40][C:35]([C:36]([O:38]C)=[O:37])=[CH:34][CH:33]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[C:22]([C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:8]=1[C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[O:1][CH2:31][C:32]1[CH:41]=[CH:40][C:35]([C:36]([OH:38])=[O:37])=[CH:34][CH:33]=1)=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]([F:21])([F:19])[F:20])(=[O:23])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 256687Methyl 4-(bromomethyl)benzoateHCID 11773771[4-(3-Hydroxyphenyl)-8-(Trifluoromethyl)Quinolin-3-yl](Phenyl)Methanone

Product 1

HCID 11261037HCID 11261037, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 4-(3-hydroxyphenyl)-8-(trifluoromethyl)quinolin-3-yl](phenyl)methanone (Example 42, 1.0 g, 2.5 mmol), methyl 4-bromomethylbenzoate (0.57 g, 2.5 mmol) and K2CO3 (1.38 g, 10 mmol) in acetone (25 ml) was heated to reflux. After 2 hr, the reaction was cooled, filtered and concentrated. The resulting oil was taken up into THF/MeOH (20 ml) and 2N NaOH (2 ml) was added and the reaction was refluxed. After 2 hr, the reaction was cooled, poured into 2N HCl and extracted with EtOAc. The EtOAc was dried concentrated and the product was purified by column chromatography (eluent 40% EtOAc/hexane) to give the desired product as a foam (1.00 g, Yield=77%); MS (ESI) m/z 528 ([M+H]+); 1H NMR (DMSO) δ 12.97 (s, 1H), 9.14 (s, 1H), 8.33 (d, 1H, J=6.6 Hz), 7.94-7.88 (m, 3H), 7.76 (t, 1H, J=8.0 Hz), 7.63 (d, 2H, J=7.1 Hz), 7.54-7.47 (m, 1H), 7.46 (d, 2H, J=8.5 Hz), 7.37-7.33 (m, 2H), 7.27 (t, 1H, J=7.8 Hz), 7.05-6.98 (m, 2H), 6.87 (m, 1H),

Workup

  1. temperaturethe reaction was cooled
  2. filtrationfiltered
  3. concentrationconcentrated
  4. additionwas added
  5. temperaturethe reaction was refluxed
  6. waitAfter 2 hr
  7. temperaturethe reaction was cooled
  8. additionpoured into 2N HCl
  9. extractionextracted with EtOAc
  10. dry with materialThe EtOAc was dried
  11. concentrationconcentrated
  12. customthe product was purified by column chromatography (eluent 40% EtOAc/hexane)

Sources & evidence

ORD record
ord-12aab14b058248a6b16a3f4ac23185bd
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

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