HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Aminopyridine → (S)-[3-(1-amino-ethyl)-phenyl]-pyridin-4-yl-amine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Aminopyridine | HCID 1727 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | (S)-N-Boc-1-(3-bromophenyl)ethylamine | HCID 56971804 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | (S)-[3-(1-amino-ethyl)-phenyl]-pyridin-4-yl-amine | HCID 60004117 | 103.2% |
Reaction Steps
A mixture of (S)-[1-(3-bromo-phenyl)-ethyl]-carbamic acid tert-butyl ester (3 g), 4-aminopyridine (1.88 g), Pd2(dba)3 (915 mg), di-t-butylbiphenylphosphine (298 mg), K3PO4 (4.24 g) in DME (20 mL) was stirred under reflux for 24 h. The reaction mixture was cooled down to room temperature, diluted with methylene chloride, filtered and concentrated in vacuo. The resulting residue was purified by flash chromatography using Biotage eluting with 5% MeOH in ethyl acetate to give the desired product (2.2 g) as a solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06900210B2 |
| Source dataset | uspto-grants-2005_05 |
| ORD ID | ord-73a443b1df5f4abd86a7984885efeef0 |
| Source note | uspto-grants-2005_05 |