Trifluoroacetic acid → (4-((6-(Difluoromethyl)pyridin-3-yl)methoxy)-3-methoxyphenyl)methanamine
Reaction equation
[F:1][CH:2]([F:28])[C:3]1[N:8]=[CH:7][C:6]([CH2:9][O:10][C:11]2[CH:25]=[CH:24][C:14]([CH2:15][NH:16]C(=O)OC(C)(C)C)=[CH:13][C:12]=2[O:26][CH3:27])=[CH:5][CH:4]=1.FC(F)(F)C(O)=O>ClCCl>[F:28][CH:2]([F:1])[C:3]1[N:8]=[CH:7][C:6]([CH2:9][O:10][C:11]2[CH:25]=[CH:24][C:14]([CH2:15][NH2:16])=[CH:13][C:12]=2[O:26][CH3:27])=[CH:5][CH:4]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of tert-butyl 4-((6-(difluoromethyl)pyridin-3-yl)methoxy)-3-methoxybenzylcarbamate (7.32 g, 18.56 mmol) in dichloromethane (30 ml) was added trifluoroacetic acid (15 mL, 194.70 mmol). After 2 h, the reaction mixture was concentrated, and the residue was dissolved in water (75 mL). The acidic solution was extracted with diethyl ether (50 mL). The aqueous phase was retained and made basic with concentrated ammonium hydroxide solution (50 mL). The basic aqueous phase was extracted with dichloromethane (2×100 mL). The combined organic phases were dried over magnesium sulfate, filtered, and concentrated to provide 4.54 g (83%) of (4-((6-(difluoromethyl)pyridin-3-yl)methoxy)-3-methoxyphenyl)methanamine as a yellow solid.
Workup
- concentrationthe reaction mixture was concentrated
- dissolutionthe residue was dissolved in water (75 mL)
- extractionThe acidic solution was extracted with diethyl ether (50 mL)
- extractionThe basic aqueous phase was extracted with dichloromethane (2×100 mL)
- dry with materialThe combined organic phases were dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-c2ec8f68e56c4757a9143ed3a2e44cc5
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09067914B1
Reaction notes
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