HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → 7-(2-Fluoro-4-iodo-phenylamino)-8-nitro-2,3-dihydro-thiazolo[3,2-a]pyridin-5-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2-Fluoro-4-iodoaniline | HCID 185694 | — |
| Reactant | Binap, (A+-)- | HCID 634876 | — |
| Reactant | Methanesulfonic acid, 1,1,1-trifluoro-, 2,3-dihydro-8-nitro-5-oxo-5H-thiazolo[3,2-a]pyridin-7-yl ester | HCID 58380532 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | 7-(2-Fluoro-4-iodo-phenylamino)-8-nitro-2,3-dihydro-thiazolo[3,2-a]pyridin-5-one | HCID 58380554 | 12.2% |
Reaction Steps
Trifluoro-methanesulfonic acid 8-nitro-5-oxo-2,3-dihydro-5H-thiazolo[3,2-a]pyridin-7-yl ester (0.6 g, 1.7 mmol) was reacted with 2-fluoro-4-iodo-phenylamine (0.45 g, 1.9 mmol), Pd(OAc)2 (38 mg, 0.17 mmol), BINAP (0.1 g, 0.17 mmol) and cesium carbonate (0.84 g, 2.6 mmol) in toluene (20 mL) at reflux for 3 hours to afford the crude product. Purification by column chromatography on silica gel (30% ethylacetate in hexane) afforded 90 mg of the product (12% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08466289B2 |
| Source dataset | uspto-grants-2013_06 |
| ORD ID | ord-fafa60bef2484d77bd9375886da8a00b |
| Source note | uspto-grants-2013_06 |