HuagongsheHuagongshe Chemistry Print Report · For research reference only
Pyridine → 1-[6-Chloro-1-(3,5-difluoro-phenyl)-1H-indol-3-yl]-2,2,2-trifluoro-ethanone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | (3,5-Difluorophenyl)boronic acid | HCID 2734338 | — |
| Reactant | 1-(6-Chloro-3-indolyl)-2,2,2-trifluoroethanone | HCID 22497252 | — |
| Catalyst | Cupric acetate | HCID 8895 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 1-[6-Chloro-1-(3,5-difluoro-phenyl)-1H-indol-3-yl]-2,2,2-trifluoro-ethanone | HCID 86610163 | 71% |
Reaction Steps
To a solution of 1-(6-chloro-1H-indol-3-yl)-2,2,2-trifluoro-ethanone (described in US 2004067939) in CH2Cl2 (in the presence of 0.4 nM molecular sieve) were added anhydrous Cu(OAc)2 (2 eq.), 3,5-difluorophenylboronic acid (3 eq.) and pyridine (4 eq.). The reaction mixture was stirred at RT for 16 h under an air atmosphere, filtered over decalite, washed with CH2Cl2 and concentrated in vacuo. Chromatography (hexane/EtOAc: 9:1) gave the title compound in 71% yield.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07803815B2 |
| Source dataset | uspto-grants-2010_09 |
| ORD ID | ord-44773a807ed94cf485f3a5d83708884c |
| Source note | uspto-grants-2010_09 |