Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 2a,3,4,5-Tetrahydrobenzo[cd]indol-2(1H)-one | HCID 599375 | — |
| Reactant | HCID 86758196 | HCID 86758196 | — |
| Product | HCID 22080927 | HCID 22080927 | 76% |
Reaction Steps
(2-acetoxy)ethyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole•trifluoroacetate (230 mg, 0.73 mmol) and (S)-4-bromobutyl)-2a,3,4,5-tetrahydro-1H-benz[cd]indol-2-one (185 mg, 0.6 mmol) were dissolved in dimethylformamide (5 ml). Then anhydrous potassium carbonate (280 mg, 2 mmol) was added thereto. The resulting reaction mixture was stirred at room temperature for 2 days. To the reaction mixture obtained was added ethyl acetate (50 ml), which was then washed with water (50 ml×2) and saturated saline solution, successively dried with anhydrous sodium sulfate. The ethyl acetate solution was concentrated under reduced pressure. To the resulting product were added methanol (30 ml) and triethylamine (3 ml), which was heated at 50° C. for 5 hours and then subjected to concentration again under reduced pressure to obtain a crude reaction product. Silica gel column chromatography was applied to purify the same, whereby 246 mg (yield 76%) of the above-described object compound could be obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06407112B1 |
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| Source dataset | uspto-grants-2002_06 |
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| ORD ID | ord-3ac709294a2a4b2f8d1fe9daf43243e7 |
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| Source note | uspto-grants-2002_06 |
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