HuagongsheHuagongshe Chemistry Print Report · For research reference only
Carbon Dioxide → 5-methoxy-1H-indole-7-carboxylic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Carbon Dioxide | HCID 280 | — |
| Reactant | 7-Bromo-5-methoxy-1H-indole | HCID 19804160 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Hexane | HCID 8058 | — |
| Product | 5-methoxy-1H-indole-7-carboxylic acid | HCID 59746604 | — |
Reaction Steps
A solution of 7-Bromo-5-methoxy-1H-indole (described in WO 2002028861) in THF was treated with 2 eq. of a solution of n-BuLi in n-hexane (1.6M) at 5° and after 30 min at this temperature was cooled to −75°. Dry ice (excess) was added and after 15 mins the mixture was quenched with H2O and washed with EtOAc. After acidification of the aqueous layer and extraction into CH2Cl2, evaporation gave the desired product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08084609B2 |
| Source dataset | uspto-grants-2011_12 |
| ORD ID | ord-5b555b3220984de8a2f53c54beac1c55 |
| Source note | uspto-grants-2011_12 |