2-Fluoropyridine → HCID 59255525, compound
Reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:11]=[CH:10][C:9]([CH2:12][OH:13])=[CH:8][C:7]=1[F:14].[H-].[Na+].F[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1>CN(C)C=O>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:11]=[CH:10][C:9]([CH2:12][O:13][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)=[CH:8][C:7]=1[F:14]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To an N,N-dimethylformamide solution (20 mL) of (4-[1,3]dioxolan-2-yl-3-fluoro-phenyl)-methanol (2.44 g, 12.3 mmol) described in Manufacturing Example 204-1-3 was added sodium hydride (537 mg, 14.8 mmol, 60% in oil), which was cooled to 0° C., after which 2-fluoropyridine (1.27 mL, 14.8 mmol) was added to this suspension, which was stirred for 2 hours at 60° C. The mixture was cooled to room temperature and partitioned into ethyl acetate and water. The organic layer was separated, washed with water, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:heptane=1:4) to obtain the title compound (2.17 g, 64%).
Workup
- temperatureThe mixture was cooled to room temperature
- custompartitioned into ethyl acetate and water
- customThe organic layer was separated
- washwashed with water
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationThe filtrate was concentrated under a reduced pressure
- customthe residue was purified by silica gel column chromatography (ethyl acetate:heptane=1:4)
Sources & evidence
- ORD record
- ord-a790f8a1e8bd42aabfd8e774f9cef5b0
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08841327B2
Reaction notes
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