Cesium carbonate → [4-({3-[3-Methyl-8-(Trifluoromethyl)Quinolin-4-yl]Phenoxy}Methyl)Phenyl]Acetic Acid
Reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[C:12]1[CH:13]=[C:14]([OH:18])[CH:15]=[CH:16][CH:17]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[C:19]([F:22])([F:21])[F:20].Br[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31][C:32]([OH:34])=[O:33])=[CH:27][CH:26]=1.C([O-])([O-])=O.[Cs+].[Cs+]>C(Cl)Cl>[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[C:12]1[CH:13]=[C:14]([CH:15]=[CH:16][CH:17]=1)[O:18][CH2:24][C:25]1[CH:26]=[CH:27][C:28]([CH2:31][C:32]([OH:34])=[O:33])=[CH:29][CH:30]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[C:19]([F:22])([F:20])[F:21]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
3-[3-Methyl-8-(trifluoromethyl)quinolin-4-yl]phenol (1.13 g, 3.73 mmol) and 4-bromomethylphenylacetic acid (1.02 g, 4.47 mmol) in CH2Cl2 (60 mL) is treated with Cs2CO3 (4.86 g, 14.9 mmol) and the reaction is stirred overnight. The solvent is removed and the residue dissolved in THF and 2N aq NaOH. After heating at 70° C. for 1 h, the reaction is cooled and the layers separated. The aqueous layer is further extracted with ethyl acetate. The combined organics are dried (Na2SO4) and concentrated. The residue is chromatographed eluting with 20:80 ethyl acetate:hexane and then 5:95 methanol:methylene chloride to afford the title product.
Workup
- customThe solvent is removed
- dissolutionthe residue dissolved in THF
- temperaturethe reaction is cooled
- customthe layers separated
- extractionThe aqueous layer is further extracted with ethyl acetate
- dry with materialThe combined organics are dried (Na2SO4)
- concentrationconcentrated
- customThe residue is chromatographed
- washeluting with 20:80 ethyl acetate
Sources & evidence
- ORD record
- ord-b5d2507d4be84c6eb619f3d095950bc2
- Source dataset
- uspto-grants-2009_08
- Patent number
- US07576215B2
Reaction notes
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