Cesium carbonate → Pyridin-2-YL(4-(3-(tetrahydro-2H-pyran-4-YL)pyridin-2-yloxy)phenyl)methanone
Reaction equation
F[C:2]1[C:7]([CH:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:6][CH:5]=[CH:4][N:3]=1.[OH:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)=[O:22])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN1CCCC1=O.O>[N:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[C:21]([C:18]1[CH:19]=[CH:20][C:15]([O:14][C:2]2[C:7]([CH:8]3[CH2:13][CH2:12][O:11][CH2:10][CH2:9]3)=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:16][CH:17]=1)=[O:22]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 180 °C
Procedure
A glass microwave reaction vessel was charged with 2-fluoro-3-(tetrahydro-2H-pyran-4-yl)pyridine (0.4000 g, 2.207 mmol), (4-hydroxyphenyl)(pyridin-2-yl)methanone (0.660 g, 3.31 mmol), and cesium carbonate (2.158 g, 6.62 mmol) in N-Methyl-2-pyrrolidinone (7.36 mL). The reaction mixture was stirred and heated in a Biotage Initiator microwave reactor at 180° C. for 30 min. The reaction mixture was diluted with water and extracted with dichloromethane. The organic extract was washed with water, sat NaCl, dried with magnesium sulfate, filtered, and concentrated. The crude product was purified by chromatography to give the title compound. MS (ESI, pos. ion) m/z: 361.0 (M+1). IC50 (uM) 0.5561.
Workup
- customA glass microwave reaction vessel
- extractionextracted with dichloromethane
- extractionThe organic extract
- washwas washed with water
- dry with materialdried with magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe crude product was purified by chromatography
Sources & evidence
- ORD record
- ord-dfcd981bcb7e4778b7d067114bab8919
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08637500B2
Reaction notes
Loading…