5-Fluoro-indolyl-3-propylazide → 5-Fluoro-indolyl-3-propylamine
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](C(N=[N+]=[N-])CC)=[CH:5]2>[Pd].C(O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([NH:7][CH2:6][CH2:5][CH3:4])=[CH:5]2Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 5-fluoro-indolyl-3-propylazide (8 g, 0.037 mol) and 10% palladium on carbon in ethanol was hydrogenated at 50 psi for 16 hours. The catalyst was filtered and the solvent removed under vacuum. The celite was washed with methanol (300 ml) and the solvent was removed under vacuum. Chromatography (15% methanol-methylene chloride plus ammonium hydroxide) afforded 4.33 g (61%) of product as a yellow solid: mp 82-84.5° C.
Workup
- filtrationThe catalyst was filtered
- customthe solvent removed under vacuum
- washThe celite was washed with methanol (300 ml)
- customthe solvent was removed under vacuum
Sources & evidence
- ORD record
- ord-81c9fd9dac2a4cb9b8e3e7d862316920
- Source dataset
- uspto-grants-2000_09
- Patent number
- US06121307
Reaction notes
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