Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | Sulfoxonium, trimethyl-, iodide (1:1) | HCID 74498 | — |
| Reactant | HCID 69693966 | HCID 69693966 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 69694285 | HCID 69694285 | — |
Reaction Steps
To a suspension of trimethylsulfoxonium iodide (400 mg, 1.83 mmol) in DMSO (25 mL) at 0° C. was added NaH (60%, 73 mg, 1.83 mmol). After 30 min., 3-{3-[6-(1-methanesulfonyl-1-methyl-ethyl)-quinolin-8-yl]-phenyl}-2-(4-methanesulfonyl-phenyl)-acrylic acid methyl ester from Step 2 (688 mg, 1.22 mmol) was added and the resulting reaction mixture stirred for 18 h at 21° C., then diluted with water and ethyl acetate. The organic extracts were washed (H2O, brine), dried (MgSO4), filtered and concentrated. Purification by flash chromatography (eluting with toluene/acetone, 80:20) provided the 2-{3-[6-(1-methanesulfonyl-1-methyl-ethyl)-quinolin-8-yl]-phenyl}-1-(4-methanesulfonyl-phenyl)-cyclopropanecarboxylic acid methyl ester compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06919353B2 |
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| Source dataset | uspto-grants-2005_07 |
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| ORD ID | ord-1c8ddb215fe848fe9764fac6b64429bd |
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| Source note | uspto-grants-2005_07 |
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