Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | Sulfoxonium, trimethyl-, iodide (1:1) | HCID 74498 | — |
| Reactant | HCID 66720614 | HCID 66720614 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 59334503 | HCID 59334503 | 76% |
Reaction Steps
Under nitrogen atmosphere, to a suspension of sodium hydride (290 mg, 7.25 mmol) in dimethyl sulfoxide (45 mL) was added trimethylsulfoxonium iodide (1.73 g, 7.86 mmol) at 0° C., and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added a solution of ethyl (2E)-3-(7-fluoro-2-methyl-2H-indazol-4-yl)acrylate (1.50 g, 6.04 mmol) in dimethyl sulfoxide (15 mL) at 0° C., and the mixture was stirred at 70° C. for 27 hr. Water was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=15/85-+50/50) to give the title compound (1.20 g, yield 76%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08110585B2 |
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| Source dataset | uspto-grants-2012_02 |
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| ORD ID | ord-e12169f794774e0da6829e6d3b3b8fd9 |
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| Source note | uspto-grants-2012_02 |
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