Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | (3-Methoxyphenyl)boronic acid | HCID 2734370 | — |
| Reactant | tert-butyl 8-bromo-2-methyl-2,3-dihydrothieno[2,3-f][1,4]oxazepine-4(5H)-carboxylate | HCID 67958981 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Water 1,2-dimethoxyethane | HCID 18180031 | — |
| Product | HCID 67959087 | HCID 67959087 | 78.4% |
Reaction Steps
A mixed solution of tert-butyl 8-bromo-2-methyl-2,3-dihydrothieno[2,3-f][1,4]oxazepine-4(5H)-carboxylate (348 mg), (3-methoxyphenyl)boronic acid (198 mg), dichlorobis(triphenylphosphine)palladium (35 mg) and potassium carbonate (415 mg) in DME-water (1:1, 10 mL) was stirred at 85° C. for 1.5 hr under a nitrogen stream. The reaction solution was cooled to room temperature, water was added, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (solvent gradient; 0→10% ethyl acetate/hexane) to give the title compound (294 mg, 78%) as a colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08916549B2 |
|---|
| Source dataset | uspto-grants-2014_12 |
|---|
| ORD ID | ord-0a0e9e5ae3a54a8cb3bd17756af4eb5b |
|---|
| Source note | uspto-grants-2014_12 |
|---|