HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 3-Biphenyl-4-ylpyridin-2-amine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 1,1'-Biphenyl-4-yl-boronic acid | HCID 151253 | — |
| Reactant | 2-Amino-3-bromopyridine | HCID 817700 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 3-Biphenyl-4-ylpyridin-2-amine | HCID 65454950 | 65.5% |
Reaction Steps
A mixture of 2M aqueous sodium carbonate solution (6.64 mL), tetrakis(triphenylphosphine)palladium(0) (0.512 g), biphenyl-4-ylboronic acid (2.28 g) and 3-bromopyridin-2-amine (1.532 g) in dehydrated THF (30 mL) was heated under reflux overnight. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give a solid. The obtained solid was crystallized from toluene, diisopropyl ether and acetonitrile to give the title compound (1.428 g) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09150591B2 |
| Source dataset | uspto-grants-2015_10 |
| ORD ID | ord-a63c0b0ced404e94a0675fe534bc27b0 |
| Source note | uspto-grants-2015_10 |