HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1748006Generated: October 30, 2026
Sodium Carbonate Decahydrate → 4-(2-Aminopyridin-3-yl)phenol
https://huagongshe.com/reaction/1748006
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate Decahydrate | HCID 151402 | — |
| Reactant | 2-Amino-3-bromopyridine | HCID 817700 | — |
| 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-Aminopyridin-3-yl)phenol | HCID 66748477 | 86.3% |
Reaction Steps
A mixture of sodium carbonate decahydrate (86.0 g), tetrakis(triphenylphosphine)palladium(0) (7.76 g), (4-((tert-butyldimethylsilyl)oxy)phenyl)boronic acid (40 g) and 3-bromopyridin-2-amine (26.9 g) in DME (500 mL) and water (50 mL) was stirred at 90° C. for 24 hr. After cooling to room temperature, the aqueous layer was removed. The organic layer was filtered with NH-silica gel cartridge, and washed with EtOAc. The filtrate was concentrated in vacuo. The residue was recrystallized from EtOAc-IPE to give the title compound (25.0 g) as a pale yellow solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09150591B2 |
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| Source dataset | uspto-grants-2015_10 |
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| ORD ID | ord-c3dfd2fdb8464484aedecd4cfbc1ec4d |
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| Source note | uspto-grants-2015_10 |
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