Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | (3-Acetamidophenyl)boronic acid | HCID 157274 | — |
| Reactant | N-(7-Bromo-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide | HCID 23113867 | — |
| Catalyst | Tetrakis(triphenylphosphine)palladium | HCID 11979704 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | HCID 23114018 | HCID 23114018 | 86% |
Reaction Steps
A solution of N-(7-bromo-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide (321 mg, 0.7 mmol) obtained in Example 35, (3-(acetylamino)phenyl)boronic acid (188 mg, 0.7 mmol), palladium(0) tetrakis(triphenylphosphine) (40.5 mg, 0.035 mmol), and an aqueous 2 N sodium carbonate solution (1.05 mL) in dimethoxyethane (2.1 mL)-ethanol (0.7 mL) was reacted with heating at 150° C. for 5 minutes in a microwave reactor. The reaction solution was cooled to room temperature, diluted with water, and extracted with ethyl acetate. The filtrate was washed with saturated brine and dried over sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to obtain 308 mg (yield: 86%) of the title compound. Melting point: 247-248° C. (ethyl acetate-hexane).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07465815B2 |
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| Source dataset | uspto-grants-2008_12 |
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| ORD ID | ord-536db43fc7734414b38e31acc4e1acc7 |
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| Source note | uspto-grants-2008_12 |
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