HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → HCID 67252274, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 6-Chloro-3-pyridinecarbonitrile | HCID 5152094 | — |
| Reactant | Ethyl 2-(1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate | HCID 58292549 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 67252274 | HCID 67252274 | 89.5% |
Reaction Steps
To a mixture of ethyl 2-(1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (2 g, 8 mmol, 1 eq.) and 6-chloronicotinonitrile (2.78 g, 20 mmol, 2.5 eq.) in 50 ml DMF was added cesium carbonate (7.82 g, 24 mmol, 3 eq.). The reaction was stirred at room temperature overnight. The starting material was gone but no right mass was observed. The reaction was then quenched by water, extracted with EtOAc, washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The crude was purified by column chromatography on silica gel (DCM/methanol=39:1 to 19:1) to give colorless oil (2.52 g, yield 89%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08343944B2 |
| Source dataset | uspto-grants-2013_01 |
| ORD ID | ord-ef2464e1aa1c48f8b261dc1c67f291e8 |
| Source note | uspto-grants-2013_01 |