Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 3,5-Dimethylisoxazole-4-boronic acid | HCID 2734346 | — |
| Reactant | HCID 66684913 | HCID 66684913 | — |
| Catalyst | Tetrakis(triphenylphosphine)palladium | HCID 11979704 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 66685360 | HCID 66685360 | 94.2% |
Reaction Steps
To a 25 mL RB flask fitted with a magnetic stirrer was charged with Toluene (1 mL). To the stirred solvent were added (3,5-dimethyl-1,2-oxazol-4-yl)boronic acid (0.059 g, 0.42 mmol), ethyl 3-(2-bromo-4-methoxyphenyl)propanoate (0.08 g, 0.28 mmol), sodium bicarbonate (0.5 mL, 2M solution) in ethanol (1 mL) under argon atmosphere. After addition, the reaction mixture was purged with argon for 15 minutes. To the reaction mixture was added tetrakis (triphenylphosphine) palladium (0) (0.016 g, 0.01 mmol) and purged with argon for 10 minutes. After addition, the reaction mixture was heated at 95° C. for 5 h under argon atmosphere. After completion of the reaction, the reaction mixture was quenched with water (10 mL) and extracted with ethyl acetate (10 mL). The organic layer was washed with water (5 mL) and brine solution (5 mL). The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The crude product (0.08 g, yield: 94.10%) was taken for next step with out purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09278915B2 |
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| Source dataset | uspto-grants-2016_03 |
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| ORD ID | ord-daf7c6bf495147bf88bc04962d2b1943 |
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| Source note | uspto-grants-2016_03 |
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