Diethyl Ether → 2-(pyridin-3-yl)-1H-indole

HRID 1980861Notes

Reaction equation

HRID 1980861 reaction equation
C(OC(=O)C1C=CC(S)=CC=1)C.[H-].[Na+].CS(OCC[C:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[NH:24][C:23]=1[C:31]1[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=1)(=O)=O.CCOCC>CN(C)C=O>[N:33]1[CH:34]=[CH:35][CH:36]=[C:31]([C:23]2[NH:24][C:25]3[C:30]([CH:22]=2)=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:32]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 24758Sodium hydrideHCID 10845149ethyl 4-mercaptobenzoateHCID 20400823HCID 20400823, compound

Product 1

HCID 6066772-(pyridin-3-yl)-1H-indole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of 5.9 g of p-mercaptobenzoic acid ethyl ester (prepared according to the procedure found in J. Chem. Soc., 1963, 1947-1954) in 30 ml of dimethylformamide is added dropwise to a slurry of 1.55 g of 50% sodium hydride (dispersion in mineral oil) in 30 ml of dimethylformamide. This mixture is stirred at room temperature for 0.5 hour under nitrogen atmosphere, and added dropwise to a solution of 9.78 g of 3-(2-methylsulfonyloxyethyl)-2-(3-pyridyl)-indole in 60 ml of dimethylformamide at -10°. This mixture is stirred at room temperature overnight and poured into 1 liter of ice-water. This is extraced several times with ether. The ether extract is washed with water, dried over MgSO4 and evaporated in vacuo to give 3-[2-(4-ethoxycarbonylphenylthio)-ethyl]-2-(3-pyridyl-indole.

Workup

  1. stirringThis mixture is stirred at room temperature overnight
  2. extractionThe ether extract
  3. washis washed with water
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-41c3cb2698274a8d8835044743b50c6f
Source dataset
uspto-grants-1985_04
Patent number
US04511573

Reaction notes

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