Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Binap, (A+-)- | HCID 634876 | — |
| Reactant | HCID 57447746 | HCID 57447746 | — |
| Reactant | 7-Chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine | HCID 57447747 | — |
| Reactant | HCID 57447748 | HCID 57447748 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Catalyst | (1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium | HCID 6505921 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 59799080 | HCID 59799080 | 86% |
Reaction Steps
7-Chloro-6-[2,2-dimethyl-3-(tetrahydro-pyran-2-yloxy)-propylamino]-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine Mix 7-chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethanesulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (1.277 g, 3.0 mmol), 2,2-dimethyl-3-(tetrahydro-pyran-2-yloxy)-propylamine (843 mg, 4.5 mmol), palladium acetate (135 mg, 0.6 mmol), BINAP (1.308 g, 2.1 mmol), bis(dibenzylideneacetone)palladium (0) (275 mg, 0.3 mmol) and cesium carbonate (1.955 g, 6.0 mmol) in anhydrous toluene (75 mL), degas, heat at 90° C. for 16 h. Filter off solid through Celite®, concentrate and purify (silica gel chromatography, eluting with 1:7 EtOAc:hexanes) to give the title compound (1.190 g, 86%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07981882B2 |
|---|
| Source dataset | uspto-grants-2011_07 |
|---|
| ORD ID | ord-d4aba0e613cd4e5e94e9fe0aed81e71a |
|---|
| Source note | uspto-grants-2011_07 |
|---|
