HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tris(furan-2-yl)phosphane → 2-Fluoro-4-[4-methyl-5-(2-{3-methyl-4-[(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)methoxy]phenyl}ethyl)thien-2-yl]benzonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tris(furan-2-yl)phosphane | HCID 521585 | — |
| Reactant | 4-Bromo-2-fluorobenzonitrile | HCID 736029 | — |
| Reactant | Tributyl[4-methyl-5-(2-{3-methyl-4-[(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)methoxy]phenyl}ethyl)thien-2-yl]stannane | HCID 21986389 | — |
| Catalyst | 1,5-Diphenylpenta-1,4-dien-3-one;palladium | HCID 154270 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 2-Fluoro-4-[4-methyl-5-(2-{3-methyl-4-[(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)methoxy]phenyl}ethyl)thien-2-yl]benzonitrile | HCID 21986300 | — |
Reaction Steps
A mixture of tributyl[4-methyl-5-(2-{3-methyl-4-[(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)methoxy]phenyl}ethyl)thien-2-yl]stannane (intermediate 100, 0.037 g) and 2-fluoro-4-bromobenzonitrile (0.011 g) in tetrahydrofuran (2 ml) was treated with palladium bis(dibenzylideneacetone) (0.0035 g) and trifuranyl phosphine (0.0013 g) and the resulting mixture stirred at reflux for 3 hours. The solvent was removed and the residue purified by Biotage® chromatography using a mixture of petroleum ether:ethyl acetate (4:1) as eluent to give the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07091237B2 |
| Source dataset | uspto-grants-2006_08 |
| ORD ID | ord-29ab68ec7fbd4c80a56aeb3f91a16063 |
| Source note | uspto-grants-2006_08 |