Methylamine → 7-(2,4-dichloro-phenyl)-2-methyl-2H-indazole-3-carboxylic acid methylamide

HRID 902561Notes

Reaction equation

HRID 902561 reaction equation
C[O:2][C:3]([C:5]1[N:6]([CH3:22])[N:7]=[C:8]2[C:13]=1[CH:12]=[CH:11][CH:10]=[C:9]2[C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=1[Cl:21])=O.[CH3:23][NH2:24]>CO>[CH3:23][NH:24][C:3]([C:5]1[N:6]([CH3:22])[N:7]=[C:8]2[C:13]=1[CH:12]=[CH:11][CH:10]=[C:9]2[C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=1[Cl:21])=[O:2]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 597023207-(2,4-dichloro-phenyl)-2-methyl-2H-indazole-3-carboxylic acid methyl ester

Product 1

HCID 597023637-(2,4-dichloro-phenyl)-2-methyl-2H-indazole-3-carboxylic acid methylamideYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 7-(2,4-dichloro-phenyl)-2-methyl-2H-indazole-3-carboxylic acid methyl ester (35b; 0.050 g, 0.15 mmol) in 4 mL of a 2 M solution of methylamine in methanol was stirred for 6 d, then concentrated to a white solid. Column chromatography (0→45% EtOAc/hexanes) afforded of 7-(2,4-dichloro-phenyl)-2-methyl-2H-indazole-3-carboxylic acid methylamide (35d; 0.044 g; 88%).

Workup

  1. concentrationconcentrated to a white solid

Sources & evidence

ORD record
ord-75e21a4f96674bf3835b0e952b77747d
Source dataset
uspto-grants-2008_04
Patent number
US07365211B2

Reaction notes

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