HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1991868Generated: October 30, 2026
HCID 66676088, compound → 5-tert-butyl-6-nitro-1H-indole
https://huagongshe.com/reaction/1991868
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | HCID 66676088 | HCID 66676088 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 5-tert-butyl-6-nitro-1H-indole | HCID 57470207 | 69.3% |
Reaction Steps
To a solution of 4-tert-butyl-5-nitro-2-trimethylsilanylethynyl-phenylamine (25 g, 86 mmol) in DMF (100 mL) was added CuI (8.2 g, 43 mmol) under a nitrogen atmosphere. The mixture was heated at 135° C. in a sealed pressure flask overnight, cooled down to room temperature and filtered through a short plug of Celite. The filter cake was washed with EtOAc. The combined filtrate was washed with water, dried over Na2SO4 and concentrated. The crude product was purified by column chromatography (10-20% ethyl acetate/hexane) to provide 5-tert-butyl-6-nitro-1H-indole as a yellow solid (13 g, 69%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07645789B2 |
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| Source dataset | uspto-grants-2010_01 |
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| ORD ID | ord-3eede9c7a361404eb636b900d9c39cd0 |
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| Source note | uspto-grants-2010_01 |
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