HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanol → HCID 59003101, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Isopropyl 5-[acetyl-(3,5-bistrifluoromethylbenzyl)amino]-8-bromo-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylate | HCID 59003154 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Catalyst | Di-tert-butyl(2',4',6'-tris(propan-2-yl)-(1,1'-biphenyl)-2-yl)phosphane | HCID 11618717 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 59003101 | HCID 59003101 | 30.5% |
Reaction Steps
Combine isopropyl-5-[acetyl-(3,5-bistrifluoromethylbenzyl)amino]-8-bromo-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylate (0.100 g, 0.168 mmol), palladium acetate (0.001 g, 0.0033 mmol), 2-di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl (0.002 g, 0.0041 mmol), cesium carbonate (0.082 g, 0.252 mmol), and methanol (0.03 mL, 0.67 mmol) in toluene (1 mL) in a 10 mL microwave vessel and irradiate the mixture at 110° C. for 30 min (45 W). Dilute the mixture with ethyl acetate (20 mL), filter through Celite® and remove the solvent under reduced pressure. Purify the residue using chromatography on silica gel, eluting with hexanes/ethyl acetate (60:40), to provide the title compound as a white solid (0.028 g, 30%): ESI MS 547 (M+H)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07749992B2 |
| Source dataset | uspto-grants-2010_07 |
| ORD ID | ord-38d6d3fa19ed4ae7bd2fee4ed63b8e70 |
| Source note | uspto-grants-2010_07 |