Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 5-Nitroindazole | HCID 21501 | — |
| Reactant | Pivaloyl chloride | HCID 62493 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 59799766 | HCID 59799766 | 79% |
Reaction Steps
A 4 L 3-neck round bottom flask fitted with a nitrogen inlet and mechanical stirrer was charged with a solution of 5-nitroindazole (80.0 g, 0.49 mol) in tetrahydrofuran (1 L). The mixture was cooled to 0° C. and triethylamine (85.4 mL, 0.61 mol) was added. To the mixture was added pivaloyl chloride (63.4 mL, 0.52 mol) dropwise over a period of 15 minutes. The reaction was allowed to warm to 20° C. over a period of 2 hours. The reaction was filtered and concentrated to a dark red oil. To the oil was added methylene chloride (60 mL). The resulting slurry was stirred vigorously, giving a white precipitate that was isolated by filtration. The solid was dried in a vacuum oven at 40° C. overnight to afford the title compound (95 g, 79%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08071779B2 |
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| Source dataset | uspto-grants-2011_12 |
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| ORD ID | ord-600e16c6c8f24095bc7b06aee0e4e64e |
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| Source note | uspto-grants-2011_12 |
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