Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 2-Amino-3-bromo-5-fluoropyridine | HCID 16126434 | — |
| Reactant | 4-Cyclohexyloxy-benzeneboronic acid | HCID 22289818 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | HCID 66747890 | HCID 66747890 | 81.4% |
Reaction Steps
Tetrakis(triphenylphosphine)palladium(0) (54.5 mg) was added to a suspension of 3-bromo-5-fluoropyridin-2-amine (300 mg), 4-(cyclohexyloxy)phenylboronic acid (449 mg) and sodium carbonate (333 mg) in DME (15 mL) and water (3 mL) and the mixture was stirred at 100° C. under nitrogen for 2 hr. Water and EtOAc were added and the organic layer was separated, washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with EtOAc in hexane) and washed with IPE to give the title compound (366 mg) as a yellow solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08778934B2 |
|---|
| Source dataset | uspto-grants-2014_07 |
|---|
| ORD ID | ord-d60cadc90e2b4ccbb9ee59f2dbf64679 |
|---|
| Source note | uspto-grants-2014_07 |
|---|
