HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2035809Generated: October 30, 2026
Sodium Carbonate → 4-(2-Amino-5-chloropyridin-3-yl)phenol
https://huagongshe.com/reaction/2035809
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 3-Bromo-5-chloropyridin-2-amine | HCID 2763971 | — |
| Reactant | 4-(tert-Butyldimethylsilyloxy)phenylboronic Acid (contains varying amounts of Anhydride) | HCID 11107815 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | 4-(2-Amino-5-chloropyridin-3-yl)phenol | HCID 66748004 | — |
| Product | 3-(4-{[Tert-butyl(dimethyl)silyl]oxy}phenyl)-5-chloropyridin-2-amine | HCID 66748550 | — |
Reaction Steps
A mixture of sodium carbonate (4.09 g), tetrakis(triphenylphosphine)palladium(0) (0.668 g), 4-(tert-butyldimethylsilyloxy)phenylboronic acid (6.32 g) and 3-bromo-5-chloropyridin-2-amine (4.00 g) in DME (100 mL) and water (20 mL) was stirred at 80° C. overnight. Silica gel was added and the mixture was concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with EtOAc in hexane) to give 4-(2-amino-5-chloropyridin-3-yl)phenol (3.05 g) as a pale yellow solid and 3-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-5-chloropyridin-2-amine (1.55 g) as a yellow solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08575154B2 |
|---|
| Source dataset | uspto-grants-2013_11 |
|---|
| ORD ID | ord-338e77853b014eb9a4b17b887d29b64c |
|---|
| Source note | uspto-grants-2013_11 |
|---|
