Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Cyclopropylboronic acid | HCID 2760897 | — |
| Reactant | HCID 68578594 | HCID 68578594 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | HCID 68578388 | HCID 68578388 | 75.7% |
Reaction Steps
A mixture of tert-butyl 9-bromo-6-fluoro-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (400 mg, 1.16 mmol), cyclopropylboronic acid (298 mg, 3.47 mmol), saturated aqueous sodium carbonate solution (6 ml), and tetrakis(triphenylphosphine)palladium(0) (36.1 mg, 0.0313 mmol) in dimethoxyethane (10 ml) was stirred under a nitrogen atmosphere at 90° 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 (270 mg, 75.7%) 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-bc84524a13c14eceba3a9b00d02d4fc2 |
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| Source note | uspto-grants-2012_08 |
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