Cesium carbonate → N-(4-(2'-(Trifluoromethyl)-3,4'-bipyridin-2-yloxy)phenyl)pyridin-2-amine
Reaction equation
F[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[NH:24][C:25]1[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O.O>[F:15][C:14]([F:17])([F:16])[C:10]1[CH:9]=[C:8]([C:7]2[C:2]([O:31][C:28]3[CH:27]=[CH:26][C:25]([NH:24][C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][N:18]=4)=[CH:30][CH:29]=3)=[N:3][CH:4]=[CH:5][CH:6]=2)[CH:13]=[CH:12][N:11]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
A mixture of 2-fluoro-2′-(trifluoromethyl)-3,4′-bipyridine (200 mg, 0.83 mmol), 4-(pyridin-2-ylamino)phenol (185 mg, 0.99 mmol) and cesium carbonate (323 mg, 0.99 mmol) in DMSO (3.3 mL) was heated to 80° C. for 4 h. The mixture was cooled to room temperature, diluted with H2O and filtered. The solids were washed with H2O and air-dried. The solids were suspended in sat aq. NaHCO3 and extracted with CH2Cl2 (3×). The combined organics were dried over Na2SO4, filtered and concentrated. The residue was purified using column chromatography (EtOAc/Hexanes=0→40%) to give the title compound. MS (ESI, pos. ion) m/z: 409 (M+1). IC50 (uM) 0.022.
Workup
- temperatureThe mixture was cooled to room temperature
- filtrationfiltered
- washThe solids were washed with H2O
- customair-dried
- extractionextracted with CH2Cl2 (3×)
- dry with materialThe combined organics were dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified
Sources & evidence
- ORD record
- ord-971dc04cbeaa4158aa406f73c623671b
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08637500B2
Reaction notes
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