HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → 3-(5-Bromo-2-(4-phenethylthiazol-2-ylamino)pyridin-4-ylthio)-5-chloroisonicotinonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 3,5-Dichloropyridine-4-carbonitrile | HCID 11137599 | — |
| Reactant | 5-Bromo-2-(4-phenethylthiazol-2-ylamino)pyridine-4-thiol | HCID 178527727 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | 3-(5-Bromo-2-(4-phenethylthiazol-2-ylamino)pyridin-4-ylthio)-5-chloroisonicotinonitrile | HCID 86634774 | 49.2% |
Reaction Steps
A flask was charged with 5-bromo-2-(4-phenethylthiazol-2-ylamino)pyridine-4-thiol (0.040 g, 0.10 mmol), 3,5-dichloroisonicotinonitrile (0.019 g, 0.11 mmol), Cs2CO3 (0.037 g, 0.11 mmol), and DMSO (2 mL). The reaction mixture was stirred at ambient temperature overnight, then quenched with water, extracted with EtOAc, dried, and concentrated. The crude material was purified by flash chromatography to provide the desired product (0.026 g, 48% yield) as a yellow solid. 1H NMR (CDCl3) δ 8.74 (d, 2H), 8.39 (s, 1H), 7.16-7.30 (m, 5H), 6.68 (s, 1H), 6.33 (s, 1H), 2.85-2.92 (m, 4H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08022222B2 |
| Source dataset | uspto-grants-2011_09 |
| ORD ID | ord-643023c9a1584667b838e04424a27ecd |
| Source note | uspto-grants-2011_09 |