Table 1.
Conditions of indole nitrogen alkylation and ester hydrolysis.
| Entry | Reactant | R-Br | Base | T (°C) | Time (h) | Product | Yield (%) |
|---|---|---|---|---|---|---|---|
| 1 | 1 | Allyl-Br | KOH (3.0 mmol/0.1 mL·H2O) | 20 | 2.0 | 2 | 85 |
| 2 | 1 | Benzyl-Br | KOH (3.0 mmol/0.1 mL·H2O) | 20 | 2.0 | 3 | 94 |
| 3 | 1 | Amyl-Br | KOH (3.0 mmol/0.1 mL·H2O) | 20 | 8.0 | 4/9 | 60/30 |
| 4 | 2 | - | KOH (6.0 mmol/1.0 mL·H2O) | 60 | 1.0 | 5 | 95 |
| 5 | 3 | - | KOH (6.0 mmol/1.0 mL·H2O) | 60 | 1.0 | 6 | 97 |
| 6 | 4 | - | KOH (6.0 mmol/1.0 mL·H2O) | 60 | 1.0 | 7 | 90 |
| 7 | 1 | Allyl-Br | NaOEt (6.0 mmol)/EtOH | 60 | 2 | 5 | 35 |
| 8 | 1 | Benzyl-Br | NaOEt (6.0 mmol)/EtOH | 60 | 2 | 6 | 40 |
| 9 | 1 | Amyl-Br | NaOEt (6.0 mmol)/EtOH | 60 | 2 | 9 | 90 |