HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → Tert-butyl 2-(6-(5-bromo-1-methyl-2-oxo-1,2-dihydropyridin-3-ylamino)pyridin-2-yloxy)ethyl(methyl)carbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2-(tert-Butoxycarbonyl(methyl)amino)-ethyl 4-methylbenzenesulfonate | HCID 21581156 | — |
| Reactant | HCID 178479984 | HCID 178479984 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | Tert-butyl 2-(6-(5-bromo-1-methyl-2-oxo-1,2-dihydropyridin-3-ylamino)pyridin-2-yloxy)ethyl(methyl)carbamate | HCID 118116879 | 22.1% |
Reaction Conditions
| Temperature | 100 °C |
|---|
Reaction Steps
A mixture of 112b (3.3 g, 10 mmol), 5-Bromo-3-(6-hydroxypyridin-2-ylamino)-1-methylpyridin-2(1H)-one 101a (7.4 g, 25 mmol) and Cs2CO3 (4.1 g, 12.5 mmol) in DMF (40 mL) was stirred at 100° C. for 4 h. The mixture partitioned between EA and water. The organic layer was separated, dried over Na2SO4, filtered and concentrated to give tert-butyl 2-(6-(5-bromo-1-methyl-2-oxo-1,2-dihydropyridin-3-ylamino)pyridin-2-yloxy)ethyl(methyl)carbamate 112c (1.0 g, 22%) as a yellow solid. ESI-LCMS: m/z=454.9
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09260415B2 |
| Source dataset | uspto-grants-2016_02 |
| ORD ID | ord-9811cc2079f245bbba64d8e6fb9698d9 |
| Source note | uspto-grants-2016_02 |