HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → 2-(4-(3-chlorobenzyloxy)-5-fluoro-1-methyl-1H-indol-3-yl)-N-methyl acetamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1-(Bromomethyl)-3-chlorobenzene | HCID 69838 | — |
| Reactant | 2-(5-fluoro-4-hydroxy-1-methyl-1H-indol-3-yl)-N-methylacetamide | HCID 58304007 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | 2-(4-(3-chlorobenzyloxy)-5-fluoro-1-methyl-1H-indol-3-yl)-N-methyl acetamide | HCID 58303987 | 82% |
Reaction Steps
A mixture of 33-6 (40 mg, 0.17 mmol), 1-(bromomethyl)-3-chlorobenzene (35 mg, 0.17 mmol) and Cesium carbonate (166 mg, 0.51 mmol) in acetonitrile (20 mL) was refluxed for 2 h. After cooled to room temperature, the mixture was filtered and the filtrate was evaporated under vacuum. The resulting residue was purified by Preparative TLC (petroleum ether/ethyl acetate=1:3) to give 33-7 (50 mg, 82%) as a white solid. LRMS: calc 360.1 and found: 361.1 [M+1].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08912220B2 |
| Source dataset | uspto-grants-2014_12 |
| ORD ID | ord-6bba1bcb2d674554b66b5cc5b8cb522b |
| Source note | uspto-grants-2014_12 |