Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 2-Bromoethyl methyl ether | HCID 80972 | — |
| Reactant | HCID 72207560 | HCID 72207560 | — |
| Catalyst | Tetrabutylammonium Iodide | HCID 67553 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 89666806 | HCID 89666806 | — |
Reaction Steps
3-Methoxy-5-nitro-1H-indazole (97 mg), 1-bromo-2-methoxyethane (70 μl, and TBAI (2 mg) were added to a DMF (1 ml) suspension containing sodium hydride (60% in oil) (24 mg) under ice cooling, followed by stirring at 100° C. for 1 hour. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layers were washed with water and saturated saline and dried over anhydrous sodium sulfate. Then, the solvent was distilled away under reduced pressure, and the obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=1:0 to 1:1). A 3-methoxy-1-(2-methoxyethyl)-5-nitro-1H-indazole (50 mg) was thus obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09051310B2 |
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| Source dataset | uspto-grants-2015_06 |
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| ORD ID | ord-b9fb69d30fba4eea9da58af908d7bc33 |
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| Source note | uspto-grants-2015_06 |
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