HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 434Generated: October 26, 2026
3-Bromoanisole → 1-(3-Methoxyphenyl)-2-methyl-6-(trifluoromethoxy)indole
https://huagongshe.com/reaction/434
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 3-Bromoanisole | HCID 16971 | — |
| Reactant | 2-Methyl-6-(trifluoromethoxy)-1H-indole | HCID 12180669 | — |
| Reagent | Sodium t-butoxide | HCID 23676156 | — |
| Catalyst | 2-(Di-tert-butylphosphino)biphenyl | HCID 2734215 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | 1-(3-Methoxyphenyl)-2-methyl-6-(trifluoromethoxy)indole | HCID 18438947 | 65.49% |
Reaction Steps
EN04773-51, _Buchwald coupling,_ ** _J. Med. Chem. 2009, page 3846-3854 (exactly same reaction)._** The indole from 4773-41, 1-bromo-3-methoxybenzenee,Pd2(dba)3, JohnPhos and KOtBu were dissolved in toluene. The mixture was warmed at 120 °C for 1h and ~65% conversion was observed on NMR*(see attached NMR). Reaction seems to work fine and assumed better yield than in 4773-50. This could be due to that bromides generally perform better than iodines in the Buchwald coupling. This test reaction was thrown away.
Provenance & Evidence
| Source dataset | 750 AstraZeneca ELN dataset |
|---|
| ORD ID | ord-5f9307492f2b4cadaa0478f3250edc2b |
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| Source note | 750 AstraZeneca ELN dataset |
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