7-[5-Nitro-6-(trifluoromethyl)-2-pyridyl]-7-azabicyclo[2.2.1]heptane → 6-(7-Azabicyclo[2.2.1]heptan-7-yl)-2-(trifluoromethyl)pyridin-3-amine
Reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([N:14]2[CH:18]3[CH2:19][CH2:20][CH:15]2[CH2:16][CH2:17]3)=[N:8][C:9]=1[C:10]([F:13])([F:12])[F:11])([O-])=O>[Pd]>[CH:15]12[N:14]([C:7]3[N:8]=[C:9]([C:10]([F:13])([F:11])[F:12])[C:4]([NH2:1])=[CH:5][CH:6]=3)[CH:18]([CH2:17][CH2:16]1)[CH2:19][CH2:20]2Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
A flask charged with 7-[5-nitro-6-(trifluoromethyl)-2-pyridyl]-7-azabicyclo[2.2.1]heptane (530 mg, 1.845 mmol) and 10% Pd/C (53 mg, 0.4980 mmol) was flushed with nitrogen followed by evacuating under vacuum. Ethanol (6 mL) was added under inert atmosphere and the flask fitted with a hydrogen balloon. After 16 h of vigorous stirring the Pd/C was removed by filtration and solvent was removed under reduced pressure. The crude material was purified via silica gel chromatography (0-10% ethyl acetate in hexanes) to provide 6-(7-azabicyclo[2.2.1]heptan-7-yl)-2-(trifluoromethyl)pyridin-3-amine (381 mg, 80% yield). 1H NMR (400.0 MHz, DMSO-d6) δ 7.17 (d, J=8.9 Hz, 1H), 6.97 (d, J=8.9 Hz, 1H), 5.03 (s, 2H), 4.29 (s, 2H), 1.59 (t, J=3.4 Hz, 4H), 1.37 (d, J=6.7 Hz, 4H).
Workup
- customwas flushed with nitrogen
- customby evacuating under vacuum
- additionEthanol (6 mL) was added under inert atmosphere
- customthe flask fitted with a hydrogen balloon
- customwas removed by filtration and solvent
- customwas removed under reduced pressure
- customThe crude material was purified via silica gel chromatography (0-10% ethyl acetate in hexanes)
Sources & evidence
- ORD record
- ord-8ea2221303604b669d41aa76d32e5f8c
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08314239B2
Reaction notes
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