HuagongsheHuagongshe Chemistry Print Report · For research reference only
Indole → Aldisine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Indole | HCID 798 | — |
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 1-Methylindole | HCID 11781 | — |
| Reactant | Phosphorus Pentoxide-Methanesulfonic Acid | HCID 86584057 | — |
| Reactant | HCID 178507349 | HCID 178507349 | — |
| Product | Aldisine | HCID 3085877 | — |
Reaction Steps
Starting with the commercially available 2-indolecarboxylic acid, condensation with the ethyl ester of β-alanine in the presence of EDCI and DMAP, provided the indole 4. Methylation of the indole nitrogen with MeI and K2CO3 proceeded in near quantitative yields, rendering the N-methyl indole, which was used for the synthesis of 3. Hydrolysis of esters 4 and 5 followed by the P2O5/MeSO3H mediated cyclization provided the key intermediate aldisine derivatives 8 and 9.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07385055B2 |
| Source dataset | uspto-grants-2008_06 |
| ORD ID | ord-4c8cbafb971d410e8d145e2866d1e668 |
| Source note | uspto-grants-2008_06 |