5-Chloro-1H-indole-2-carboxylic acid → methyl N-[(5-chloro-1H-indol-2-yl)carbonyl]glycinate

HRID 651085Notes

Reaction equation

HRID 651085 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:7])[CH2:5][NH2:6].[Cl:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([C:18](O)=[O:19])=[CH:12]2>C(OCC)(=O)C>[CH3:2][O:3][C:4](=[O:7])[CH2:5][NH:6][C:18]([C:13]1[NH:14][C:15]2[C:11]([CH:12]=1)=[CH:10][C:9]([Cl:8])=[CH:17][CH:16]=2)=[O:19]

Participants

4

Reactant 2

HCID 826935-Chloro-1H-indole-2-carboxylic acidHCID 122755Glycine methyl ester hydrochloride

Product 1

HCID 4893740methyl N-[(5-chloro-1H-indol-2-yl)carbonyl]glycinate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Glycine methyl ester hydrochloride (50 mmol) and 5-chloro-1H-indole-2-carboxylic acid (50 mmol) were coupled according to procedure A, substituting the following workup: the reaction mixture was stirred in ethyl acetate (250 mL), hexanes (50 mL) and 1N NaOH (50 mL) and the suspension was filtered. The solid was washed with 1N NaOH, 1N HCl, with water, ethyl acetate, and dried: Yield 11.5 g, 86%; mp 252-254° C. with decomposition;

Workup

  1. filtrationhexanes (50 mL) and 1N NaOH (50 mL) and the suspension was filtered
  2. washThe solid was washed with 1N NaOH, 1N HCl, with water, ethyl acetate
  3. customdried

Sources & evidence

ORD record
ord-9f25ca8098ba4c8793049f4b20820569
Source dataset
uspto-grants-2001_08
Patent number
US06277877B1

Reaction notes

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