Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 6-bromo-4-nitro-1H-indazole | HCID 24728059 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 58267997 | HCID 58267997 | — |
| Product | 6-bromo-2-methyl-4-nitro-2H-indazole | HCID 90308703 | — |
Reaction Steps
60% Sodium hydride (including 40% liquid paraffin as an additive) (213 mg) was added to a solution of 6-bromo-4-nitro-1H-indazole (901 mg) in DMF (19 ml) in an ice bath. Subsequently, the reaction solution was stirred at 0° C. for 15 minutes, then methyl iodide (0.35 ml) was added, and the reaction solution was allowed to react at room temperature for 11 hours. The reaction solution was poured into water, and the deposited precipitate was filtrated to obtain a crude product. The crude product was purified by column chromatography on silica gel (developing solvent:hexane/ethyl acetate) to obtain 6-bromo-1-methyl-4-nitro-1H-indazole and 6-bromo-2-methyl-4-nitro-2H-indazole as a yellow solid, respectively.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09145414B2 |
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| Source dataset | uspto-grants-2015_09 |
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| ORD ID | ord-cbd09c06eb044f8cad96773192b6ea41 |
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| Source note | uspto-grants-2015_09 |
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