Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Methyl 3-bromobenzoate | HCID 12070 | — |
| Reactant | Binap, (A+-)- | HCID 634876 | — |
| Reactant | HCID 118699713 | HCID 118699713 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 118699712 | HCID 118699712 | 69% |
Reaction Steps
A mixture of 6,7,8,9-Tetrahydrothieno[3,2-c]-2,7-naphthyridine (3.0 g, 15.77 mmol, prepared as previously described), methyl-3-bromobenzoate (3.90 g, 18.14 mmol), palladium(II)acetate (354 mg, 1.577 mmol), racemic BINAP (982 mg, 1.577 mmol) and cesium carbonate (7.19 g, 22.08 mmol) in toluene (270 ml) was heated at 100° C. with stirring for 18 hours. Upon cooling to room temperature, the insolubles were filtered off (celite) and washed with EtOAc. The washing was combined with the filtrate and concentrated. Elution through a flash column (silica gel 60, 230-400 mesh, EtOAc) gave the product as a yellow glass (3.54 g, 69%). MS (APCl): (M+1)+=325;
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09255096B1 |
|---|
| Source dataset | uspto-grants-2016_02 |
|---|
| ORD ID | ord-1aaaef26583f4ea6b9fcb5f9abee7d42 |
|---|
| Source note | uspto-grants-2016_02 |
|---|