The results of optimization of reaction conditions for compound 4j synthesisa.
Entry | Solvent | Temperature (°C) | Time (h) | Yieldb (%) |
---|---|---|---|---|
1 | Ethanol | Reflux | 24 | 75 |
2 | Water | Reflux | 24 | 50 |
3 | Methanol | Reflux | 24 | 61 |
4 | DMSO | 100 | 24 | 52 |
5 | DMF | 100 | 24 | 52 |
6 | Dioxane | 100 | 24 | 28 |
7 | THF | Reflux | 24 | 40 |
8 | Acetonitrile | Reflux | 24 | 38 |
9 | Ethyl acetate | Reflux | 24 | 30 |
10 | Chloroform | Reflux | 24 | 0 |
11 | Toluene | 100 | 24 | 0 |
12 | Solvent-free | 100 | 24 | 0 |
13 | Ethanol | RT | 24 | 0 |
14 | Ethanol | 40 | 24 | 0 |
15 | Ethanol | 60 | 24 | 34 |
16 | Ethanol | Reflux | 24 | 75 |
17 | Ethanol | Reflux | 10 | 75 |
18 | Ethanol | Reflux | 2 | 75 |
19 | Ethanol | Reflux | 1.5 | 60 |
20 | Ethanol | Reflux | 1 | 41 |
Reaction conditions: 5-chloroisatin (1 mmol), 3-amino-4-bromo-1H-pyrazole (1 mmol), tert-butyl isocyanide (1 mmol), solvent (3 mL).
Isolated yield in the presence of CeCl3·7H2O catalyst (30 mol%).