HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → 2-(2-(triethylsilyl)-5-(trifluoromethyl)-1H-indol-3-yl)ethanol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Lithium Chloride | HCID 433294 | — |
| Reactant | 4-(Triethylsilyl)-3-butyn-1-ol | HCID 2760694 | — |
| Reactant | 2-Iodo-4-(trifluoromethyl)aniline | HCID 2783322 | — |
| Catalyst | Palladium Chloride | HCID 24290 | — |
| Catalyst | Ferrocene-1,1'-bis-(diphenylphosphine) | HCID 635956 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 2-(2-(triethylsilyl)-5-(trifluoromethyl)-1H-indol-3-yl)ethanol | HCID 66832009 | 61.3% |
Reaction Steps
2-(2-(triethylsilyl)-5-(trifluoromethyl)-1H-indol-3-yl)ethanol was prepared according to method D Step II with 2-iodo-4-(trifluoromethyl)aniline (1.0 g; 3.48 mmol), 4-(triethylsilyl)but-3-yn-1-ol (0.807 mL; 3.83 mmol), Bis(diphenylphosphino)ferrocene]palladium(II) chloride (0.142 g; 0.174 mmol), lithium chloride (0.147 g; 3.48 mmol) and sodium carbonate (0.738 g; 6.97 mmol) in DMF (10 mL). The crude mixture was purified by flash chromatography on silica gel (eluent 2 to 40% ethyl acetate in heptane) to afford 0.733 g (61%) of 2-(2-(triethylsilyl)-5-(trifluoromethyl)-1H-indol-3-yl)ethanol as a yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09284271B2 |
| Source dataset | uspto-grants-2016_03 |
| ORD ID | ord-9f91656bdf814a65b79f4f5818bc3787 |
| Source note | uspto-grants-2016_03 |