HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 518480Generated: October 28, 2026
Sodium Bicarbonate → 4-[5-(2,4-Difluorophenoxy)-2-methylsulfonylpyrimidin-4-yl]-6-methylfuro[2,3-c]pyridin-7-one
https://huagongshe.com/reaction/518480
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 4-Chloro-5-(2,4-difluorophenoxy)-2-methylsulfonylpyrimidine | HCID 118021544 | — |
| Reactant | 4-Bromo-2-fluoro-6-methylfuro[2,3-c]pyridin-7-one | HCID 118022459 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | 1,4-Dioxane--water (1/1) | HCID 21886435 | — |
| Product | 4-[5-(2,4-Difluorophenoxy)-2-methylsulfonylpyrimidin-4-yl]-6-methylfuro[2,3-c]pyridin-7-one | HCID 118022006 | 79.2% |
Reaction Steps
A mixture of 4-chloro-5-(2,4-difluorophenoxy)-2-methylsulfonylpyrimidine (155 mg, 0.48 mmol), 4-bromo-2-fluoro-6-methylfuro[2,3-c]pyridin-7-one (120 mg, 0.44 mmol), NaHCO3 (92 mg, 1.1 mmol), Pd(dppf)Cl2 (32 mg, 10%) in dioxane/H2O (4 mL/200 uL) was bubbled with nitrogen for 7 min. The sealed vial was stirred at 70° C. for 8 h. LCMS analysis showed complete consumption of the limiting reagent. The reaction mixture was filtered through a short plug of celite; the celite plug was washed with DCM. The filtrate was concentrated in vacuo. The resulting residue was purified by silica gel column chromatography using a gradient of EtOAc (10 to 100%) in DCM to afford the title compound (151 mg, 79%) as a yellow solid. LCMS (M+H)+=434.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09115114B2 |
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| Source dataset | uspto-grants-2015_08 |
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| ORD ID | ord-67071b2386a248eba5b3cf6b3802b01f |
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| Source note | uspto-grants-2015_08 |
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