HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Hydroxide → 5-Ethynyl-3-(2-pyrrolidinylethyl)-1H-indole
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Hydroxide | HCID 14797 | — |
| Reactant | 3-(2-Pyrrolidinylethyl)-1-(p-toluenesulfonyl)-5-(triethylsilylethynyl)-indole | HCID 15838487 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | 5-Ethynyl-3-(2-pyrrolidinylethyl)-1H-indole | HCID 15838488 | 66.2% |
Reaction Steps
3-(2-Pyrrolidinylethyl)-1-(p-toluenesulfonyl)-5-(triethylsilylethynyl)-indole (Example 6a, 130 mg, 0.26 mmol) was mixed with 5% potassium hydroxide in methanol (20 mL) and stirred at reflux for up to 48 h. The solvent was evaporated to about 4 mL, poured into dichloromethane (40 mL), washed with brine (40 mL), dried over sodium sulfate and evaporated. Chromatography on silica gel (dichloromethane/methanol/ammonium hydroxide 50:7:1) gave the title compound as a yellow oil (41 mg, 66%). HRMS-FAB+ for C16H19N2 : calculated MH+ : 239.15483, found MH+ : 239.15766.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05856510 |
| Source dataset | uspto-grants-1999_01 |
| ORD ID | ord-7d1c50edf0694fdbb24102c6de3b1847 |
| Source note | uspto-grants-1999_01 |