Potassium Hydroxide → 5-Ethynyl-3-(2-pyrrolidinylethyl)-1H-indole

HRID 342029Notes

Reaction equation

HRID 342029 reaction equation
[N:1]1([CH2:6][CH2:7][C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]#[C:18][Si](CC)(CC)CC)[CH:15]=3)[N:10](S(C3C=CC(C)=CC=3)(=O)=O)[CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[K+]>CO>[C:17]([C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH:9]=[C:8]2[CH2:7][CH2:6][N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)#[CH:18]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 158384873-(2-Pyrrolidinylethyl)-1-(p-toluenesulfonyl)-5-(triethylsilylethynyl)-indole

Product 1

HCID 158384885-Ethynyl-3-(2-pyrrolidinylethyl)-1H-indoleYield 66.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

  1. temperatureat reflux for up to 48 h
  2. customThe solvent was evaporated to about 4 mL
  3. additionpoured into dichloromethane (40 mL)
  4. washwashed with brine (40 mL)
  5. dry with materialdried over sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-7d1c50edf0694fdbb24102c6de3b1847
Source dataset
uspto-grants-1999_01
Patent number
US05856510

Reaction notes

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