Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | N-Fluorobenzenesulfonimide | HCID 588007 | — |
| Reactant | Lithium diisopropylamide | HCID 2724682 | — |
| Reactant | HCID 67777605 | HCID 67777605 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 67776841 | HCID 67776841 | 48.5% |
Reaction Steps
To a solution of 6-(cyclopropylmethoxy)-2-(4-{[tris(1-methylethyl)silyl]oxy}phenyl)-2H-indazole (218 mg) in THF (2.5 mL) was added dropwise a THF solution (1.11 M, 0.59 mL) of lithiumdiisopropylamide at −78° C. under an argon atmosphere, and the mixture was stirred for 30 min. To the reaction mixture was added N-fluorobenzenesulfonimide (236 mg) at −78° C., and the mixture was stirred at 0° C. for 1.5 hr. Water was added to the reaction mixture, and the mixture was extracted twice with ethyl acetate. The combined organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound as colorless crystals (110 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08729102B2 |
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| Source dataset | uspto-grants-2014_05 |
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| ORD ID | ord-6927bdc447ee4d4f89e49d840e6306c3 |
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| Source note | uspto-grants-2014_05 |
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