HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → HCID 58118667, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1-((2-(Trimethylsilyl)ethoxy)methyl)-1,3-dihydro-2H-pyrrolo(2,3-b)pyridin-2-one | HCID 57458886 | — |
| Reactant | HCID 86650287 | HCID 86650287 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 58118667 | HCID 58118667 | — |
Reaction Steps
To a solution of 4,5-bis(bromomethyl)-2-chloropyridine from Step D (254 mg, 0.85 mmol) and 1-{[2-(trimethylsilyl)ethoxy]methyl}-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one (226 mg, 0.86 mmol, described in Intermediate 4) in DMF (8 mL) was added cesium carbonate (455 mg, 1.40 mmol). After 21 h, the reaction mixture was poured into H2O (60 mL) and extracted with EtOAc (2×60 mL). The organic layer was washed with brine (40 mL), then dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of hexanes:EtOAc—100:0 to 0:100, to give the title compound. MS: m/z=402 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08765759B2 |
| Source dataset | uspto-grants-2014_07 |
| ORD ID | ord-8346ac7cebe24e30b01185140c3a2477 |
| Source note | uspto-grants-2014_07 |