Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | (4-Methoxyphenyl)boronic acid | HCID 201262 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 66635662 | HCID 66635662 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 66635696 | HCID 66635696 | 57.1% |
Reaction Steps
(S)-(1-(7-(3-Methylphenyl)-3-iodo-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)pyrrolidin-2-yl)methanol (22 mg), 4-methoxyphenylboronic acid (17 mg) and tetrakis(triphenylphosphine)palladium (10 mg) are added to toluene (10 mL), ethanol (3 mL) and 1 N NaHCO3 aqueous solution (1.5 mL) and stirred overnight at 90° C. 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 (12 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-03ce5d82f94e418f8edf07929a0bef51 |
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| Source note | uspto-grants-2015_03 |
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