HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → 3-(5-Bromo-2-(4-phenethylthiazol-2-ylamino)pyridin-4-yloxy)-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)pyridin-4-ol | HCID 178516464 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | 3-(5-Bromo-2-(4-phenethylthiazol-2-ylamino)pyridin-4-yloxy)-5-chloroisonicotinonitrile | HCID 86634780 | 7.3% |
Reaction Steps
A mixture of 5-bromo-2-(4-phenethylthiazol-2-ylamino)pyridin-4-ol (0.060 g, 0.16 mmol), 3,5-dichloroisonicotinonitrile (0.030 g, 0.18 mmol) and Cs2CO3 (0.057 g, 0.18 mmol) was stirred in DMSO (2 mL) at 100° C. overnight. The solution was cooled, quenched with water, extracted with EtOAc, dried, and concentrated. The crude material was purified by flash chromatography gave the desired product (0.006 g, 7% yield) as a white solid. 1H NMR (CDCl3) δ 8.55 (s, 1H), 8.50 (s, 1H), 8.27 (s, 1H), 7.12-7.26 (m, 5H), 6.87 (s, 1H), 6.37 (s, 1H), 2.89 (bs, 4H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08022222B2 |
| Source dataset | uspto-grants-2011_09 |
| ORD ID | ord-2a973e9399f741eba6784f809ddad006 |
| Source note | uspto-grants-2011_09 |