Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1,3,4-Thiadiazole, 2-amino-5-methyl- | HCID 66949 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | 3,5-Dibromo-1-methylpyridin-2(1H)-one | HCID 3614350 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 86684506 | HCID 86684506 | 73.1% |
Reaction Steps
A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 5-methyl-1,3,4-thiadiazol-2-amine (1.15 g, 10.0 mmol), 3,5-dibromo-1-methylpyridin-2(1H)-one (4.00 g, 15.0 mmol), Pd2(dba)3 (916 mg, 1.0 mmol), Xantphos (1.16 g, 2.0 mmol), Cs2CO3 (6.52 g, 20.0 mmol), and dioxane (50 mL). After three cycles of vacuum/argon flush, the mixture was heated at 100° C. for 3 h. It was then cooled to room temperature and filtered. The filtrate was evaporated under reduced pressure and the resulting residue was purified by silica-gel column chromatography eluting with 20:1 dichloromethane/methanol to afford 267a (2.2 g, 73%) as white solid. MS-ESI: [M+H]+ 301.2
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08716274B2 |
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| Source dataset | uspto-grants-2014_05 |
|---|
| ORD ID | ord-7c61d70c49484d17a7dbd75c18cf4b90 |
|---|
| Source note | uspto-grants-2014_05 |
|---|
