HuagongsheHuagongshe Chemistry Print Report · For research reference only
Indole → 5-(2,2,2-trifluoroethoxy)-1H-indole-3-carboxylic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Indole | HCID 798 | — |
| Reactant | Flurothyl | HCID 9528 | — |
| Reactant | 3-Methyl-4-nitrophenol | HCID 17412 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | Ethanol, 2,2,2-trifluoro-, 1-(4-methylbenzenesulfonate) | HCID 67942 | — |
| Reactant | Phenolate | HCID 119047 | — |
| Solvent | Hexamethylphosphoramide | HCID 12679 | — |
| Product | 5-(2,2,2-trifluoroethoxy)-1H-indole-3-carboxylic acid | HCID 57646517 | — |
Reaction Steps
5-(2,2,2-trifluoroethoxy)-1H-indole-3-carboxylic acid was prepared following the procedure reported in Synthesis (1980) 727. 3-methyl-4-nitrophenol (Aldrich) was deprotonated with sodium hydride in HMPA and the resulting phenolate alkylated with 2,2,2-trifluoroethyl tosylate (Aldrich). The resulting trifluoroethyl ether was then converted to the indole using the Batcho-Leimgruber protocol. Formylation and oxidation as described in herein gave the title compound as an off-white solid. MS (m/e) 260.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08114891B2 |
| Source dataset | uspto-grants-2012_02 |
| ORD ID | ord-82562456717e4bc0a0b3eb602f1d20b7 |
| Source note | uspto-grants-2012_02 |