4-Toluenesulfonyl chloride → methyl 1-tosyl-1H-indole-4-carboxylate

HRID 1982465Notes

Reaction equation

HRID 1982465 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]2[CH:7]=[CH:8][NH:9][C:10]=2[CH:11]=[CH:12][CH:13]=1)=[O:4].[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1>C(Cl)Cl.C(N(CC)CC)C>[CH3:1][O:2][C:3]([C:5]1[C:6]2[CH:7]=[CH:8][N:9]([S:20]([C:17]3[CH:18]=[CH:19][C:14]([CH3:24])=[CH:15][CH:16]=3)(=[O:22])=[O:21])[C:10]=2[CH:11]=[CH:12][CH:13]=1)=[O:4]

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 2733668methyl 1H-indole-4-carboxylate

Product 1

HCID 10947463methyl 1-tosyl-1H-indole-4-carboxylateYield 89.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

A solution of 21 g of indole-4-carboxylic-acid-methylester in 100 ml of methylene-chloride, 24.9 ml of triethylamine and 7.34 g of 4-dimethyl-aminopyridine is proportionately mixed at 0° C. with 34.2 g of p-toluene-sulfonic-acid-chloride. After 16 h at 0° C., the mixture is diluted with methylene chloride, washed neutral with saturated sodium bicarbonate solution and NaCl solution, and the solvent is distilled off in vacuum. 35.37 g of 1-tosylindole-4-carboxylic-acid-methylester with a m.p. of 145°-147° C. (diisopropylether) is obtained.

Workup

  1. washwashed neutral with saturated sodium bicarbonate solution and NaCl solution
  2. distillationthe solvent is distilled off in vacuum

Sources & evidence

ORD record
ord-88f8e6b159bb4b37a94f7ebce146bce7
Source dataset
uspto-grants-1986_06
Patent number
US04596808

Reaction notes

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