Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Binap, (A+-)- | HCID 634876 | — |
| Reactant | HCID 67284465 | HCID 67284465 | — |
| Reactant | 3,3-Dimethyl-6-morpholinoindoline | HCID 67284858 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 50940107 | HCID 50940107 | — |
Reaction Steps
Prepared according to procedure T using 4-(3,3-dimethylindolin-6-yl)morpholine (0.2 g, 0.86 mmol), 7,9-dichloro-3,3-dimethyl-2,3-dihydro-1H-cyclopenta[b]-quinoline (0.434 g, 1.72 mmol), cesium carbonate (0.561 g, 1.72 mmol), Pd2(dba)3 (0.079 g, 0.086 mmol) and (±) BINAP (0.084 g, 0.129 mmol) in 1,4-dioxane (2 mL). After HPLC purification 7-chloro-9-(3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-indol-1-yl)-3,3-dimethyl-2,3-dihydro-1H-cyclopenta[b]-quinoline was obtained. 1H NMR (500 MHz, DMSO-d6) δ ppm 8.02 (1H, d, J=9.0 Hz), 7.86 (1H, m), 7.68 (1H, m), 7.06 (1H, m), 6.38 (1H, m), 5.73 (1H, s), 3.86 (2H, d, J=0.5 Hz), 3.73 (2H, s), 3.62 (4H, dd, J=5.4, 4.4 Hz), 3.06 (1H, m), 2.84-2.94 (4H, m), 1.96 (1H, m), 1.33 (12H, m). Mass Spectrum (ESI) m/e=463 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08765940B2 |
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| Source dataset | uspto-grants-2014_07 |
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| ORD ID | ord-d21e5b5f411a4dfcb4c570a67add6899 |
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| Source note | uspto-grants-2014_07 |
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