Optimization of reaction conditionsa.
Entry | Base | Solvent | Time | Yieldb (%) |
---|---|---|---|---|
1 | Cs2CO3 | CH3CN | 58 h | 12 |
2 | K2CO3 | CH3CN | 18 h | 15 |
3 | Na2CO3 | CH3CN | 18 h | 12 |
4 | NaOH | CH3CN | 18 h | 30 |
5 | DABCO·6H2O | CH3CN | 27 h | 16 |
6 | DBU | CH3CN | 33 h | 45 |
7 | NEt3 | CH3CN | 3 h | 32 |
8 | TMG | CH3CN | 5 min | 87c |
9 | TMG | CHCl3 | 4 h | 82 |
10 | TMG | Toluene | 4 h | 74c |
11 | TMG | EtOAc | 20 min | 58 |
12d | TMG | CH3CN | 5 min | 95c |
13e | TMG | CH3CN | 5 min | 80c |
Unless otherwise noted, the reactions were conducted with 0.15 mmol 1a with 2.0 equivalents of 2a in the presence of 2.0 equivalents of base in 0.8 mL of specified solvent at 60 °C.
Isolated yields obtained by column chromatography.
Isolated yields obtained by filtration of the precipitate.
2.2 equivalents of 2a were used.
2.4 equivalents of 2a were used. DABCO = 1,4-diazabicyclo[2.2.2]octane; DBU = 1,8-diazabicyclo[5.4.0]undec-7-ene; TMG = 1,1,3,3-tetramethylguanidine.