HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → 1-cyclopropylmethyl-6-ethoxy-2-(4-nitro-phenyl)-1H-indole
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Bromomethylcyclopropane | HCID 81503 | — |
| Reactant | 6-ethoxy-2-(4-nitro-phenyl)-1H-indole | HCID 59030425 | — |
| Solvent | Water | HCID 962 | — |
| Product | 1-cyclopropylmethyl-6-ethoxy-2-(4-nitro-phenyl)-1H-indole | HCID 59030426 | 88% |
Reaction Steps
6-Ethoxy-2-(4-nitro-phenyl)-1H-indole (4.5 g, 16 mmol), Cs2CO3 (7.8 g, 24 mmol), DMF (23 mL), and bromomethylcyclopropane (1.8 mL, 18 mmol) were stirred at 80° C. in a sealed tube for 16 hours. The reaction mixture was diluted with H2O and extracted with EtOAc. The organic layer was washed with H2O and brine and then dried and concentrated. Purification by silica gel chromatography (1:1 CH2Cl2/hexane) provided 1-cyclopropylmethyl-6-ethoxy-2-(4-nitro-phenyl)-1H-indole (4.73 g, 88%) as an orange solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07772271B2 |
| Source dataset | uspto-grants-2010_08 |
| ORD ID | ord-30a61c31ea61401787f5f6a3dc3872f8 |
| Source note | uspto-grants-2010_08 |