Methyl iodide → Methyl 1-(1-methylethyl)-1H-indole-5-carboxylate

HRID 564975Notes

Reaction equation

HRID 564975 reaction equation
[CH:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13]([OH:15])=[O:14])=[CH:10][CH:11]=2)[CH:6]=[CH:5]1)([CH3:3])[CH3:2].[H-].[Na+].[CH3:18]I>CN(C)C=O>[CH:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13]([O:15][CH3:18])=[O:14])=[CH:10][CH:11]=2)[CH:6]=[CH:5]1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 21194436178053-59-3

Product 1

HCID 15550263Methyl 1-(1-methylethyl)-1H-indole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2.20 g (8.97 mmol) of isopropyl 1-isopropyl-5-indolecarboxylate, 100 ml of 2N sodium hydroxide solution and 100 ml of ethanol was refluxed for an hour. The solvent was then distilled off under reduced pressure. Thereafter water was added to the residue and the resulting mixture was acidified with conc. hydrochloric acid. The precipitated solid was filtered and dried under reduced pressure to give 2.00 g of crude 1-isopropyl-5-indole-carboxylic acid. The reaction was carried out in a manner similar to Reference Example 4 using 2.00 g of the crude 1-isopropyl-5-indolecarboxylic acid, 0.44 g (11.1 mmol) of 60% sodium hydride, 2.87 g (20.2 mmol) of methyl iodide and 50 ml of dimethyl-formamide. Thus, 1.64 g (84.2%; yield based on isopropyl 1-isopropyl-5-indolecarboxylic acid) was obtained.

Workup

  1. customThus, 1.64 g (84.2%; yield based on isopropyl 1-isopropyl-5-indolecarboxylic acid)
  2. customwas obtained

Sources & evidence

ORD record
ord-938dcd2aeffe4867beed5a237aa35cde
Source dataset
uspto-grants-2001_01
Patent number
US06169107A

Reaction notes

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