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 118116346 | HCID 118116346 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 118116911 | HCID 118116911 | 28.4% |
Reaction Steps
A mixture of 114e (440 mg, 1.79 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 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 (S)—N-(1-(6-(5-bromo-1-methyl-2-oxo-1,2-dihydropyridin-3-ylamino)pyridin-2-yl)piperidin-3-yl)acrylamide 114f (220 mg, 28%) as yellow solid. MS-ESI: [M+H]+ 433.3
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09260415B2 |
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| Source dataset | uspto-grants-2016_02 |
|---|
| ORD ID | ord-1b0a947a22d84cf5abd6dab43a9a1b86 |
|---|
| Source note | uspto-grants-2016_02 |
|---|
