Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Imidazole | HCID 795 | — |
| Reactant | tert-Butyldimethylsilyl chloride | HCID 28928 | — |
| Reactant | HCID 10274527 | HCID 10274527 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 21877099 | HCID 21877099 | 72.9% |
Reaction Steps
A solution of 2-{4-[(3,5-dibromophenyl)sulfanyl]-3,5-diethyl-1H-pyrazol-1-yl}ethanol (1.3 g, 3 mmol) (Example 93) in dimethylformamide (3 ml) was treated with imidazole (270 mg, 4 mmol) and tert-butyl(chloro)dimethylsilane (500 mg, 3.3 mmol) and stirred at 20° C. for 15 hours. The mixture was partitioned between diethyl ether (70 ml) and citric acid solution (5% weight:volume in water, 150 ml). The aqueous layer was further extracted with diethyl ether (70 ml) and the combined organic layers were washed with brine (2×70 ml), dried over magnesium sulphate, filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel eluting with pentane:dichloromethane (1:1, by volume) to provide the title compound (1.2 g) as a colourless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06750230B2 |
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| Source dataset | uspto-grants-2004_06 |
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| ORD ID | ord-ee566148012346f1bc3d1aacc894d9b5 |
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| Source note | uspto-grants-2004_06 |
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