Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Iodoethane | HCID 6340 | — |
| Reactant | Benzyl Bromide | HCID 7498 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | Iodide Ion | HCID 30165 | — |
| Reactant | Ethyl indole-2-carboxylate | HCID 73125 | — |
| Reactant | (2,4-Bis(1,1-dimethylpropyl)phenoxy)acetic acid | HCID 83411 | — |
| Reactant | Hydride | HCID 166653 | — |
| Reactant | Potassium bis(trimethylsilyl)amide | HCID 3251421 | — |
| Reactant | Aluminium lithium hydride | HCID 21226445 | — |
| Catalyst | HCID 178418406 | HCID 178418406 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | Indole | HCID 798 | — |
Reaction Steps
Aldehyde IX is prepared from Indol-2-carboxylic acid ethyl ester I in two steps: (1) Reduction with lithium aluminium hydride or other hydride in a suitable solvent such as THF at 0° C. and (2) oxidation with an oxidizing reagent such as manganese dioxide in a solvent such as THF. Aldehyde IX can be alkylated by a suitable alkyl bromide (or iodide), such as benzyl bromide or ethyl iodide in the presence of a strong base such as sodium hydride or KHMDS in a solvent such as DMF to yield indole X. Indole X can be converted to an unsaturated acid XI in two steps: (1) Wittig reaction with a suitable reagent such as trimethyl phosphonoacetate in the presence of a base such as sodium hydride in a solvent such as THF and (2) Hydrolysis by aqueous sodium hydroxide.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06630496B1 |
|---|
| Source dataset | uspto-grants-2003_10 |
|---|
| ORD ID | ord-1ba50e4089b049edb24d60b5da4e322e |
|---|
| Source note | uspto-grants-2003_10 |
|---|
