HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → 2-[4-(tert-Butyl-dimethyl-silanyloxymethyl)-6-chloro-pyridin-2-ylamino]-thiazole-5-carbonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | 2-Chlorothiazole-5-carbonitrile | HCID 1485222 | — |
| Reactant | 4-(2-Tert-butylsilyloxypropan-2-yl)-6-chloropyridin-2-amine | HCID 131724818 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 2-[4-(tert-Butyl-dimethyl-silanyloxymethyl)-6-chloro-pyridin-2-ylamino]-thiazole-5-carbonitrile | HCID 131724819 | — |
Reaction Steps
An oven dried flask under N2 was charged with 4-(tert-butyl-dimethyl-silanyloxymethyl)-6-chloro-pyridin-2-ylamine (11-5, 0.488 g, 1.79 mmol), 2-chloro-5-cyanothiazole (1-2, 0.310 g, 2.15 mmol), cesium carbonate (0.816 g, 2.50 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.033 g, 0.040 mmol) and Xantphos (0.062 g, 0.060 mmol). Anhydrous dioxane, 6 mL, was added and the reaction was heated to reflux. After 3 hours the reaction was cooled to room temperature and stirred overnight. The reaction was diluted with water and extracted 3× with DCM. The extracts were dried over Na2SO4, filtered and concentrated. The resulting solid was triturated with ether, and filtered to afford the product as a tan solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06875767B2 |
| Source dataset | uspto-grants-2005_04 |
| ORD ID | ord-a3266913e02b4a78b83ae5f121981f20 |
| Source note | uspto-grants-2005_04 |