Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Boronic acid, (4-ethylphenyl)- | HCID 2734352 | — |
| Reactant | HCID 58280253 | HCID 58280253 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 58280144 | HCID 58280144 | — |
Reaction Steps
Add 5.2 mg (0.007 mmol) of bis(triphenylphosphine)palladium(II) chloride,. 30.6 mg (0.221 mmol) of potassium carbonate, 0.04 ml of methanol and 31 mg (0.207 mmol) of 4-ethylbenzeneboronic acid successively under argon to a solution of 70 mg (0.148 mmol) of (+)-4-{(3S)-3-[(5-bromo-6-phenylfuro[2,3-d]pyrimidin-4-yl)oxy]piperidin-1-yl}butanoic acid methyl ester in 0.4 ml of DMSO. Stir the mixture at 80° C. for a total of 3.5 h. After cooling, purify the reaction mixture directly by preparative RP-HPLC (eluent: acetonitrile/water gradient). 37.3 mg (50.6% of theory) of the target compound are isolated.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08324222B2 |
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| Source dataset | uspto-grants-2012_12 |
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| ORD ID | ord-1d6fc32abe3b4f4eb05495a6dbdc8606 |
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| Source note | uspto-grants-2012_12 |
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