Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Potassium Carbonate | HCID 11430 | — |
| Edukt | 4-Octyne | HCID 16029 | — |
| Edukt | 2-Bromo-4-fluoroaniline | HCID 242873 | — |
| Katalysator | palladium(II) acetate | HCID 167845 | — |
| Katalysator | 1,1'-Bis(di-tert-butylphosphino)ferrocene | HCID 71310544 | — |
| Lösungsmittel | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Produkt | 2-Propyl-3-propyl-5-fluoro-1H-indole | HCID 21916624 | 80,9% |
Reaktionsschritte
A 50 mL three neck flask was charged with palladium acetate (22.4 mg, 0.1 mmol), dtbpf (94 mg, 0.2 mmol), potassium carbonate (690 mg, 5 mmol), 2-bromo-4-fluoroaniline (380 mg, 2 mmol), 4-octyne (264 mg, 2.4 mmol) and NMP (10 ml). The mixture was purged with argon and heated to 130° C. After 1 hr, the reaction mixture was cooled to rt. Ethyl acetate and water were added. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic phases were washed with water, brine and dried with MgSO4. Removal of the solvents and purification of the crude by column chromatography afforded the desired product as yellow oil (355 mg, containing 4.3 wt % AcOEt). The corrected yield was 77.6%.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US07126009B2 |
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| Quelldatensatz | uspto-grants-2006_10 |
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| ORD ID | ord-ee56f80cf6cf40bfa928dffb2d2f4444 |
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| Quellennotiz | uspto-grants-2006_10 |
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