Water → Methyl 5-methoxy-1-methyl-3-(methylthio)-1H-indole-2-carboxylate

HRID 21581Notes

Reaction equation

HRID 21581 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]([C:14]([O:16][CH3:17])=[O:15])=[C:8]2[S:18][CH3:19].I[CH3:21].O>CN(C)C=O>[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH3:21])[C:9]([C:14]([O:16][CH3:17])=[O:15])=[C:8]2[S:18][CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 10538712methyl 5-methoxy-3-(methylthio)-1H-indole-2-carboxylate

Product 1

HCID 10730410Methyl 5-methoxy-1-methyl-3-(methylthio)-1H-indole-2-carboxylateYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A suspension of 60% sodium hydride in mineral oil (0.30 g, 7.5 mmol) in 3.0 mL of N,N-dimethylformamide is cooled in ice while a solution of methyl 5-methoxy-3-(methylthio)-1H-indole-2-carboxylate (1.3 g, 5.2 mmol) in 10 mL of N,N-dimethylformamide is added dropwise. The mixture is stirred for 45 minutes, then iodomethane (0.50 mL, 1.1 g, 8.0 mmol) is added in one portion. After stirring at room temperature for 8 hours, the mixture is added to 100 g of ice and water. The solid is filtered and washed with 10% methanol-water to yield 1.2 g (88%) of product. A sample purified by flash chromatography (silica gel, 25% hexane in dichloromethane elution) and recrystallized from hexane has mp 89°-91° C.

Workup

  1. additionis added dropwise
  2. stirringAfter stirring at room temperature for 8 hours
  3. filtrationThe solid is filtered
  4. washwashed with 10% methanol-water

Sources & evidence

ORD record
ord-03311f3de5584e87aa4d6b82483962f2
Source dataset
uspto-grants-1995_06
Patent number
US05424329

Reaction notes

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