5-Ethenyl-6-fluoropyridin-3-amine → 5-Ethyl-6-fluoropyridin-3-amine
Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH2:10])[C:5]([F:8])=[N:6][CH:7]=1>CO.[Pd]>[NH2:1][C:2]1[CH:3]=[C:4]([CH2:9][CH3:10])[C:5]([F:8])=[N:6][CH:7]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of the 5-amino-2-fluoro-3-vinylpyridine from Step 126c above (2.30 g, 16.6 mmol) in MeOH (50 mL) was added to a suspension of 10% palladium on activated carbon (Aldrich, 0.10 g) in MeOH (75 ml). The mixture was placed under an atmosphere of H2 (balloon) for 48 h. The catalyst was removed by filtration and the solvent was evaporated to yield the title compound as a beige solid (2.31 g, 99%): 1H NMR (CDCl3, 300 MHz) δ 1.22 (t, J=7.5 Hz, 3H), 2.58 (q, J=7.5 Hz, 2H), 6.96 (dd, J=3.0, 5.1 Hz, 1H), 7.45 (m, 1H); MS (CI/NH3) m/z 141 (M+H)+, 158 (M+NH4)+.
Workup
- customThe catalyst was removed by filtration
- customthe solvent was evaporated
Sources & evidence
- ORD record
- ord-f18e75a7be074298b61be8d4aba0b647
- Source dataset
- uspto-grants-2000_10
- Patent number
- US06133253
Reaction notes
Loading…