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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 446Erstellt: 23. Oktober 2026

3-Iodobenzyloxybenzene → 2-Methyl-1-(3-phenylmethoxyphenyl)-6-(trifluoromethoxy)indole

https://huagongshe.com/de/reaction/446

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
Edukt3-IodobenzyloxybenzeneHCID 4228019—
Edukt2-Methyl-6-(trifluoromethoxy)-1H-indoleHCID 12180669—
ReagenzSodium t-butoxideHCID 23676156—
Katalysator2-(Di-tert-butylphosphino)biphenylHCID 2734215—
KatalysatorBis(dibenzylideneacetone)palladiumHCID 9811564—
LösungsmittelTolueneHCID 1140—
Produkt2-Methyl-1-(3-phenylmethoxyphenyl)-6-(trifluoromethoxy)indoleHCID 5921672010,45%

Reaktionsbedingungen

Temperatur120 °C

Reaktionsschritte

EN04773-52, _Buchwald coupling, toluene and iodide_ The indole from 4773-25, 1-(benzyloxy)-3-iodobenzene,Pd2(dba)3, JohnPhos and KOtBu were dissolved in toluene. The mixture was warmed at 120 °C for 1h and 50% conversion was observed on NMR*(see attached NMR). The mixture was warmed further 15h at 120°C, still starting material left but the reaction mixture was directly applied to a silica column (heptane 3:1). Product was collected in fraction 22-23 (see attached NMR). Only 19.3 mg (10.45% yield) could be collected but NMR showed correct product. Test reaction with bromide was performed in 4773-53. ######################### *Small amount from reaction mixture was dissolved in CDCl3 and 1HNMR analysis was performed)

Herkunft & Nachweise

Quelldatensatz750 AstraZeneca ELN dataset
ORD IDord-055c0d9926684c29963cad751105f26e
Quellennotiz750 AstraZeneca ELN dataset