HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium fluoride → HCID 69291901, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium fluoride | HCID 25953 | — |
| Reactant | 2-Amino-5-bromopyridine | HCID 70622 | — |
| Reactant | Ethyl α-ethoxy-2,6-difluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzeneacetate | HCID 69290159 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | HCID 69291901 | HCID 69291901 | — |
Reaction Steps
A solution of (RS)-[2,6-difluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ethoxy-acetic acid ethyl ester in 1,2-dimethoxyethane was treated with 2-amino-5-bromopyridine and CsF. The reaction mixture was deoxygenated by passing a stream of argon through it. Tetrakis(triphenylphosphine)palladium(0) was added. The reaction mixture was heated to 80° for 2 days, then cooled to rt and concentrated. The crude product was isolated by flash chromatography (cyclohexane/EtOAc 2:1=>EtOAc) to give (RS)-[4-(6-amino-pyridin-3-yl)-2,6-difluoro-phenyl]-ethoxy-acetic acid ethyl ester as amorphous brown solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07129238B2 |
| Source dataset | uspto-grants-2006_10 |
| ORD ID | ord-6e93b809c45b47bcbeeab50ac6a5353a |
| Source note | uspto-grants-2006_10 |