HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 7-Methyl-1H-indole-5-carboxylic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Oxolane--water (1/1) | HCID 21881883 | — |
| Reactant | HCID 21998738 | HCID 21998738 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Water | HCID 962 | — |
| Product | 7-Methyl-1H-indole-5-carboxylic acid | HCID 15247555 | — |
Reaction Steps
A solution of 7-methyl-5-indolyl trifluoromethanesulfonate (3.19 g, 11.4 mmol), triethylamine, and 1,1′-bis(diphenylphosphino)ferrocene palladium (II) chloride (catalytic)in 9:1 THF/water was stirred under CO2 (500 psi) until HPLC indicated complete conversion. The solution was treated with water (30 mL), adjusted to pH 4-5, and extracted sequentially with ethyl acetate (100 mL) and dichloromethane (3×40 mL). The combined extracts were dried (Na2SO4), filtered, and concentrated to provide the desired product which was used in the next step without further purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06228868B1 |
| Source dataset | uspto-grants-2001_05 |
| ORD ID | ord-851d473653a544a0aa7a3560d6a62891 |
| Source note | uspto-grants-2001_05 |