Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | 1-(2-Bromoethyl)-2-chlorobenzene | HCID 2756963 | — |
| Reactant | 1,2,3,4,5,6-Hexahydro-3,9-dimethylazepino[4,5-b]indole | HCID 68560092 | — |
| Catalyst | Copper iodide | HCID 83717 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 59368162 | HCID 59368162 | 14.2% |
Reaction Steps
The title compound was prepared by following general procedure 4. 3,9-Dimethyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole (214 mg, 1.0 mmol) was taken with copper iodide (19 mg, 0.1 mmol), L-praline (23 mg, 0.2 mmol), potassium phosphate tribasic (426 mg, 2.0 mmol), 1-(2-bromoethyl)-2-chlorobenzene (219 mg, 1.0 mmol) and DMF was added, the reaction was stirred at 90° C. under argon atmosphere for 12 h and monitored by LCMS. After completion of the reaction water was added and extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and concentrated under vacuum. The crude product was purified by reverse phase chromatography to afford 50 mg of the title compound (10.7%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09409910B2 |
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| Source dataset | uspto-grants-2016_08 |
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| ORD ID | ord-2b745779186d43ed988d4e04ed4e7b38 |
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| Source note | uspto-grants-2016_08 |
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