Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 5-Indolylboronic acid | HCID 2734361 | — |
| Reactant | Ethyl 6-chloropyrazine-2-carboxylate | HCID 19084590 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 68749773 | HCID 68749773 | 55.4% |
Reaction Steps
6-Chloro-pyrazine-2-carboxylic acid ethyl ester (1.35 g, 7.23 mmol) was added to indole-5-boronic acid (1.16 g, 7.23 mmol), cesium carbonate (9.43 g, 28.9 mmol) and PdCl2(dppf).DCM (591 mg, 0.72 mmol) in 30 mL of dioxane. The mixture was degassed (evacuate in vacuo and pressurize with nitrogen), 14.5 mL of water was added and the mixture degassed. The mixture was heated at 85° C. for 2.5 h. and the mixture was allowed to cool and the layers were separated. The aqueous phase was extracted with chloroform and the combined organic layers were washed with brine, dried over sodium sulfate, filtered and evaporated. Chromatography of the residue on silica gel, eluting with ethyl acetate/pentane afforded 1.07 g of product. LC/MS: Retention time, 3.21 min; (M+H)=268.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07625889B2 |
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| Source dataset | uspto-grants-2009_12 |
|---|
| ORD ID | ord-dd9d542dd3244bb5a664ba1a8594b052 |
|---|
| Source note | uspto-grants-2009_12 |
|---|
