N-bromobutanimide → Methyl 2-(6-amino-5-bromopyridin-3-yloxy)-4-fluorobenzoate
Reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([O:8][C:9]2[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:10]=2[C:11]([O:13][CH3:14])=[O:12])=[CH:4][CH:3]=1.[Br:20]N1C(=O)CCC1=O>CN(C)C=O>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([O:8][C:9]2[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:10]=2[C:11]([O:13][CH3:14])=[O:12])=[CH:4][C:3]=1[Br:20]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A mixture of EXAMPLE 318B (1.6 g) in N,N-dimethylformamide (50 mL) was cooled to 0° C., followed by the addition of N-bromosuccinimide (1.195 g) in N,N-dimethylformamide (10 mL) solution. The reaction mixture was stirred at 0° C. for 1 hour, and quenched with ice-cold saturated NaHCO3 aqueous solution. The reaction mixture was extracted with ethyl acetate. The combined organic phase was washed with water and brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The crude material was purified using flash column purification with 30-40% ethyl acetate/hexane to provide the title compound.
Workup
- customquenched with ice-cold saturated NaHCO3 aqueous solution
- extractionThe reaction mixture was extracted with ethyl acetate
- washThe combined organic phase was washed with water and brine
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe crude material was purified
- customflash column purification with 30-40% ethyl acetate/hexane
Sources & evidence
- ORD record
- ord-c778a2bbee2d45d1b3e17cebaf3e1062
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09029404B2
Reaction notes
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