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 | 3,5-Dibromo-1-methylpyridin-2(1H)-one | HCID 3614350 | — |
| Reactant | HCID 118117179 | HCID 118117179 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 118116564 | HCID 118116564 | 22% |
Reaction Steps
A mixture of 110e (400 mg, 1.82 mmol), 3,5-dibromo-1-methylpyridin-2(1H)-one (534 mg, 2.0 mmol), Pd2(dba)3 (83 mg, 0.091 mmol), Xantphos (105 mg, 0.182 mmol) and Cs2CO3 (1.48 g, 4.55 mmol) in DMF (10 mL) was stirred at 95° C. under N2 for 7 h. The mixture was diluted with EA (50 mL) and filtered. The filtrate was washed with water, dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel chromatography (PE/EA=1/2) to give N-(2-((6-(5-bromo-1-methyl-2-oxo-1,2-dihydropyridin-3-ylamino)pyridin-2-yl)(methyl)amino)ethyl)acrylamide 110f (160 mg, 22%) as a yellow solid. ESI-LCMS: m/z=408.0
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09260415B2 |
|---|
| Source dataset | uspto-grants-2016_02 |
|---|
| ORD ID | ord-261f311a36db49bebdca2b4a41b1ff17 |
|---|
| Source note | uspto-grants-2016_02 |
|---|
