N-[4-chloro-2-fluoro-5-{2-(methoxycarbonyl)methoxy-3-pyridyloxy}phenyl]acetamide → 4-Chloro-2-fluoro-5-{2-(methoxycarbonyl)methoxy-3-pyridyloxy}aniline
Reaction equation
[Cl:1][C:2]1[C:7]([O:8][C:9]2[C:10]([O:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])=[N:11][CH:12]=[CH:13][CH:14]=2)=[CH:6][C:5]([NH:21]C(=O)C)=[C:4]([F:25])[CH:3]=1>CO.B(F)(F)F>[Cl:1][C:2]1[C:7]([O:8][C:9]2[C:10]([O:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])=[N:11][CH:12]=[CH:13][CH:14]=2)=[CH:6][C:5]([NH2:21])=[C:4]([F:25])[CH:3]=1Participants
3
Conditions
- Temperature
- 65 °C
Procedure
A mixture of 20 ml of boron trifluoride methanol complex methanol solution and 1.04 g of N-[4-chloro-2-fluoro-5-{2-(methoxycarbonyl)methoxy-3-pyridyloxy}phenyl]acetamide was stirred for 3 hours at temperature from 60 to 70° C. Thereafter, the reaction solution was concentrated, the residue was diluted with saturated aqueous sodium bicarbonate solution, and extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over magnesium sulfate, and concentrated, and the resulted residue was purified by column chromatography concentrated to obtain 0.87 g of 4-chloro-2-fluoro-5-{2-(methoxycarbonyl)methoxy-3-pyridyloxy}aniline.
Workup
- concentrationThereafter, the reaction solution was concentrated
- additionthe residue was diluted with saturated aqueous sodium bicarbonate solution
- extractionextracted with ethyl acetate
- washThe organic layer was washed with saturated saline
- dry with materialdried over magnesium sulfate
- concentrationconcentrated
- customthe resulted residue was purified by column chromatography
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-08c01d08b5014726a75735b793a947a2
- Source dataset
- uspto-grants-2003_03
- Patent number
- US06537948B1
Reaction notes
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