HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 4-Oxo-4,5-dihydrothieno[2,3-c]quinoline-7-carbonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Methyl 3-bromothiophene-2-carboxylate | HCID 2740074 | — |
| Reactant | 2-Amino-4-cyanobenzeneboronic acid hydrochloride | HCID 44118766 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 4-Oxo-4,5-dihydrothieno[2,3-c]quinoline-7-carbonitrile | HCID 57500686 | — |
Reaction Steps
Methyl-3-bromothiophene carboxylate (1.0 eq, 2.42 g, 10.95 mmol), 2-amino-4-cyanophenylboronic acid hydrochloride (1.05 eq, 2.28 g, 11.49 mmol) and cesium carbonate (2.0 eq, 7.13 g, 21.9 mmol) were suspended in dioxane (25 ml) containing 5% water. The mixture was degassed by bubbling nitrogen for 10 minutes. PdCl2(dppf) (0.05 eq, 400 mg, 0.55 mmol) was added and the mixture was stirred at reflux for 1.5 hours. The mixture was cooled down, the solid filtered, washed with dioxane, water and methanol. After drying in vacuo, 4-oxo-4,5-dihydrothieno[2,3-c]quinoline-7-carbonitrile was isolated as a solid (1.81 g, 73% yield). LCMS (ES) m/z 227 [M+1]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08168651B2 |
| Source dataset | uspto-grants-2012_05 |
| ORD ID | ord-bb101d80efe34071a394b2d19a9673fe |
| Source note | uspto-grants-2012_05 |