Potassium Carbonate → HCID 117759640, compound
Reaction equation
[CH:1]1([CH:4]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][O:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]4[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:26]=4[F:33])=[C:21]([OH:34])[CH:20]=3)[CH:12]=2)[CH2:5][C:6]([O:8]CC)=[O:7])[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].BrCC(C)(C)C.[H-].[Na+].[Cl-].[NH4+]>CN(C=O)C>[CH:1]1([CH:4]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][O:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]4[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:26]=4[F:33])=[C:21]([OH:34])[CH:20]=3)[CH:12]=2)[CH2:5][C:6]([OH:8])=[O:7])[CH2:2][CH2:3]1Participants
Conditions
- Temperature
- 90 °C
Procedure
To a solution of ethyl 3-cyclopropyl-3-(3-(((2′-fluoro-2-hydroxy-5′-methoxybiphenyl-4-yl)oxy)methyl)phenyl)propanoate (203 mg) and potassium carbonate (179 mg) in DMF (3.0 mL) was added 1-bromo-2,2-dimethylpropane (0.11 mL), and the mixture was stirred at 90° C. for 1 hr. 60% Sodium hydride (35 mg) was added at room temperature, and the mixture was stirred at 50° C. for 3 hr. To the reaction mixture was added saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (128 mg) as a brown oil.
Workup
- stirringthe mixture was stirred at 50° C. for 3 hr
- extractionthe mixture was extracted with ethyl acetate
- washThe extract was washed with saturated brine
- dry with materialdried over anhydrous sodium sulfate
- customThe solvent was evaporated under reduced pressure
- customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-ecd02a2e0c7843f68ad52f2a3dd393da
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09382188B2
Reaction notes
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