Toluene → 5-chloro-2-methyl-3-[[1-[2-(1H-pyrrol-1-yl)ethyl]piperidin-4-yl]thio]-1H-indole

HRID 36887

Reaction equation

HRID 36887 reaction equation
C1(C)C=CC=CC=1.[Cl:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([CH3:18])=[C:12]2[S:19][CH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.C(=O)([O-])[O-].[Na+].[Na+].I[CH2:33][CH2:34][N:35]1[CH:39]=[CH:38][CH:37]=[CH:36]1>O.ClCCl>[Cl:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([CH3:18])=[C:12]2[S:19][CH:20]1[CH2:25][CH2:24][N:23]([CH2:33][CH2:34][N:35]2[CH:39]=[CH:38][CH:37]=[CH:36]2)[CH2:22][CH2:21]1

Participants

6

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 117700111-(2-Iodoethyl)-1H-pyrroleHCID 152292715-chloro-2-methyl-3-(piperidin-4-ylthio)-1H-indole

Product 1

HCID 199366225-chloro-2-methyl-3-[[1-[2-(1H-pyrrol-1-yl)ethyl]piperidin-4-yl]thio]-1H-indole

Reagents, catalysts & solvents 1

HCID 21908982Water methylene chlorideSolvent

Procedure

A toluene solution (100 ml) of 5-chloro-2-methyl-3-(piperidin-4-ylthio)-1H-indole (1.09 g, prepared in Example 18), sodium carbonate (0.78 g) and 1-(2-iodoethyl)-1H-pyrrole (0.92 g, prepared according to GALEAZZI, E.; GUZMAN, A.; PINEDO, A.; SALDANA, A.; TORRE, D.; MUCHOWSKI, J. M., Can. J. Chem. (1983) 61, 454-60) is refluxed for 15 hours. The reaction mixture is taken up in a water/dichloromethane mixture. The organic phase is dried over magnesium sulfate and concentrated. The residue is chromatographed on silica gel (eluent: CH2Cl2 /MeOH:90/10) to give 5-chloro-2-methyl-3-[[1-[2-(1H-pyrrol-1-yl)ethyl]piperidin-4-yl]thio]-1H-indole (0.9 g).

Workup

  1. temperature(1983) 61, 454-60) is refluxed for 15 hours
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue is chromatographed on silica gel (eluent: CH2Cl2 /MeOH:90/10)

Sources & evidence

ORD record
ord-004b306ad62141d38d2ed9eea186b3c9
Source dataset
uspto-grants-1995_05
Patent number
US05418242

Linked notes

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