HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → 3-{[2-Chloro-4-(trifluoromethyl)phenyl](cyclopropyl)methyl}-7-[(methylsulfanyl)methyl]-1H-indole
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | 7-[(Methylsulfanyl)methyl]-1H-indole | HCID 58392187 | — |
| Reactant | [2-Chloro-4-(trifluoromethyl)phenyl](cyclopropyl)methanol | HCID 58392518 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 3-{[2-Chloro-4-(trifluoromethyl)phenyl](cyclopropyl)methyl}-7-[(methylsulfanyl)methyl]-1H-indole | HCID 58392406 | — |
Reaction Steps
2.6 ml (33.8 mmol) of trifluoroacetic acid were added to 7.07 g (28.2 mmol) of the compound from Example 150A and 5.00 g (28.2 mmol) of the compound from Example 8A in 620 ml of dichloromethane, and the mixture was stirred at RT for 2 h. It was concentrated and the residue was purified by flash chromatography on silica gel (mobile phase: toluene/ethyl acetate 98/2) and preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid) to result in 960 mg (7% of theory) of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08063234B2 |
| Source dataset | uspto-grants-2011_11 |
| ORD ID | ord-14453a4a734d4d06a7b9ff24b22a5fa9 |
| Source note | uspto-grants-2011_11 |