Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | 4-Iodo-2-(methylthio)pyrimidine | HCID 3858901 | — |
| Reactant | HCID 57891740 | HCID 57891740 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Potassium Carbonate | HCID 11430 | — |
| Product | HCID 57891678 | HCID 57891678 | — |
Reaction Steps
In a microwave reaction tube, 8-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrrolo[2,3-b]pyridine-1-sulfonyl]-quinoline (47, 70 mg, 0.16 mmol), 4-iodo-2-methylsulfanyl-pyrimidine (101 mg, 0.402 mmol), and tetrakis(triphenylphosphine)palladium(0) (9.3 mg, 0.008 mmol) were mixed in 1.0 M potassium carbonate in water (0.48 mL) and tetrahydrofuran (0.77 mL). The resulting mixture was heated at 120° C. in a CEM Discover microwave unit for 10 minutes. Ethyl acetate and water were added, and the two layers were separated. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine and dried over sodium sulfate. Concentration under reduced pressure afforded the crude material, which was purified by column chromatography (50% ethyl acetate in hexane) to yield the desired product in light yellow solid (46, 10 mg, 0.023 mmol). MS(ESI) [M+H+]+=434.0.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07605168B2 |
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| Source dataset | uspto-grants-2009_10 |
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| ORD ID | ord-72fb4323141b4a6a8a6fb910b598b605 |
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| Source note | uspto-grants-2009_10 |
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