Optimizing of the reaction conditions for the synthesis of 1aa.
![]() | |||||
---|---|---|---|---|---|
Entry | Solvent | Temperature (°C) | Catalyst loading (mg) | Time (min.) | Yieldb (%) |
1 | — | 120 | 20 | 20 | 80 |
2 c | — | 110 | 20 | 20 | 80 |
3 | — | 110 | 30 | 20 | 78 |
4 | 110 | 10 | 20 | 67 | |
5 | — | 110 | — | 20 | Trace |
6 | — | 110 | — | 120 | 45 |
7 | — | 100 | 20 | 30 | 50 |
8 | — | 90 | 20 | 60 | 40 |
9 | — | 80 | 20 | 60 | Trace |
11 | H2O | Reflux | 20 | 240 | — |
12 | EtOH | Reflux | 20 | 240 | — |
13 | n-Hexane | Reflux | 20 | 240 | Trace |
14 | EtOAc | Reflux | 20 | 240 | 35 |
15 | CH2Cl2 | Reflux | 20 | 240 | 20 |
16 | THF | Reflux | 20 | 240 | 45 |
Reaction conditions: benzaldehyde (1 mmol, 0.106 g), ke3 (1 mmol, 0.370 g), 3-(1H-indol-3-yl)-3-oxopropanenitrile (1 mmol, 0.184 g) and ammonium acetate (1.5 mmol, 0.115 g).
Related to isolated yields.
Optimal data.