Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | HCID 15691441 | HCID 15691441 | — |
| Reactant | 4-Chloro-2-ethynyl-1-methoxybenzene | HCID 23260703 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Tetrabutylammonium Fluoride | HCID 2724141 | — |
| Product | HCID 71295584 | HCID 71295584 | 25.9% |
Reaction Steps
A mixture of 4-chloro-2-ethynyl-1-methoxybenzene (255 mg, 1.5 mmol), N-(2-bromo-3-fluorophenyl)-2,2,2-trifluoroacetamide (400 mg, 1.4 mmol), Pd(PPh3)2Cl2 (30 mg, 0.04 mmol) was stirred in TBAF.3H2O (1.43 g, 7 mmol) at 110° C. for 12 hours. The reaction mixture was cooled to 25° C. and added to water, then extracted with ethyl acetate and washed with brine, dried over Na2SO4. After concentrated, the crude product of 2-(5-chloro-2-methoxyphenyl)-4-fluoro-1H-indole (100 mg, yield: 20%) was obtained. MS (M+H)+: 276/278.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09265773B2 |
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| Source dataset | uspto-grants-2016_02 |
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| ORD ID | ord-a918d2833bdd4ee99330845097d2245b |
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| Source note | uspto-grants-2016_02 |
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