Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 2-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane | HCID 5233012 | — |
| Reactant | Tert-butyl 9-bromo-2,3-dihydrobenzo[F][1,4]oxazepine-4(5H)-carboxylate | HCID 59403519 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | HCID 68579338 | HCID 68579338 | 34.9% |
Reaction Steps
A mixture of tert-Butyl 9-bromo-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (852 mg, 2.60 mmol), vinylboronic acid pinacol ester (400 mg, 2.60 mmol), saturated aqueous sodium carbonate solution (12 ml), and tetrakis(triphenylphosphine)palladium(0) (84.8 mg, 0.0734 mmol) in dimethoxyethane (15 ml) was stirred under a nitrogen atmosphere at 85° C. for 12 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1) to give the desired product (250 mg, 34.9%) as an oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08247403B2 |
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| Source dataset | uspto-grants-2012_08 |
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| ORD ID | ord-786fbebfc7564649bfb82fb684af8958 |
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| Source note | uspto-grants-2012_08 |
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