HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1009530Generated: October 31, 2026
Diethyl Ether → 1-ethyl-2-(3-hydroxy-phenyl)-6-methoxy-1H-indole-3-carbonitrile
https://huagongshe.com/reaction/1009530
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Diethyl Ether | HCID 3283 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | 3-Iodophenol | HCID 12272 | — |
| Reactant | 1-ethyl-6-methoxy-2-tributylstannanyl-1H-indole-3-carbonitrile | HCID 59424949 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 1-ethyl-2-(3-hydroxy-phenyl)-6-methoxy-1H-indole-3-carbonitrile | HCID 59426406 | 72% |
Reaction Steps
1-Ethyl-6-methoxy-2-tributylstannanyl-1H-indole-3-carbonitrile (1.0 g, 2.05 mmol), prepared in step A, is combined with 3-iodophenol (474 mg, 2.15 mmol), Pd(PPh3)2Cl2 (67 mg, 0.102 mmol), CuI (75 mg, 0.39 mmol) and THF (4.0 mL). This mixture is heated at 65° C. overnight. The reaction mixture is diluted in EtOAc, and is filtered through celite. The filtrate is concentrated and the residue is purified by silica gel chromatography (4:1, CH2Cl2/EtOAc) to yield crude product. Ether trituration yields 1-ethyl-2-(3-hydroxy-phenyl)-6-methoxy-1H-indole-3-carbonitrile (430 mg, 72%) as a yellow-white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07973069B2 |
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| Source dataset | uspto-grants-2011_07 |
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| ORD ID | ord-b628d4b61d91433ba37e98d05991e051 |
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| Source note | uspto-grants-2011_07 |
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