Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-one | HCID 21955795 | — |
| Reactant | HCID 67466678 | HCID 67466678 | — |
| Catalyst | Tetrakis(triphenylphosphine)palladium | HCID 11979704 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 67465024 | HCID 67465024 | — |
Reaction Steps
To a stirring solution of 3-(6-bromo-3-(difluoromethoxy)-2-methoxyphenoxy)-2,2-dimethylpropan-1-ol (200 mg, 0.563 mmol) in dimethylformamide (10 mL) was purged with argon for 1 h. To this cesium carbonate (548 mg, 1.689 mmol), tetrakis(triphenylphosphine) palladium(0) (32 mg, 0.028 mmol) and 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-one (175 mg, 0.675 mmol) were added and the resultant reaction mixture was heated to 80-90° C. for 3 h. The reaction mixture was cooled to RT, filtered and the filtrate was diluted with water and extracted with ethyl acetate (3×). The combined ethyl acetate layer was washed with brine and dried over anhydrous sodium sulphate and concentrated under reduced pressure. Purification of the residue by column chromatography (silica gel, 0-20% ethyl acetate in pet ether) afforded the title compound as a (50 mg, 22%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09051290B2 |
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| Source dataset | uspto-grants-2015_06 |
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| ORD ID | ord-beb92ee0f7f24aeaafd1c72d0b962e53 |
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| Source note | uspto-grants-2015_06 |
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