Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | (2H-1,3-benzodioxol-5-yl)boronic acid | HCID 2734371 | — |
| Reactant | HCID 66635660 | HCID 66635660 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 66635827 | HCID 66635827 | 91.1% |
Reaction Steps
(S)-(1-(7-(3,5-Difluorophenyl)-3-iodo-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)pyrrolidin-2-yl)methanol (40 mg), 3,4-methylenedioxyphenylboronic acid (23 mg) and tetrakis(triphenylphosphine)palladium (10 mg) are added to toluene (5 mL), ethanol (3 mL) and 1 N NaHCO3 aqueous solution (1.5 mL) and stirred at 85° C. for 4 hours under argon atmosphere. After cooling to room temperature, the reaction solvent is removed by distillation under reduced pressure. The remainder is extracted with ethyl acetate and water. The organic layer is washed with brine and dehydrated with anhydrous MgSO4. The dehydrated organic layer is concentrated by distillation under reduced pressure and purified by column chromatography to yield the target compound (36 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08975264B2 |
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| Source dataset | uspto-grants-2015_03 |
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| ORD ID | ord-cd8eb8d167b34d84bb7cca31441bc4ea |
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| Source note | uspto-grants-2015_03 |
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