Carbon Dioxide → 6-methyl-1H-indazole-5-carboxylic acid

HRID 643972Notes

Reaction equation

HRID 643972 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[CH3:11])[NH:7][N:6]=[CH:5]2.BrC1C=C2C(=CC=1F)NN=C2.C([Li])(C)(C)C.[C:28](=[O:30])=[O:29]>>[CH3:11][C:10]1[CH:9]=[C:8]2[C:4]([CH:5]=[N:6][NH:7]2)=[CH:3][C:2]=1[C:28]([OH:30])=[O:29]

Participants

5

Reactant 4

HCID 280Carbon DioxideHCID 247292595-Bromo-6-methyl-1H-indazoleHCID 468639235-Bromo-6-fluoro-1H-indazoleHCID 178418306HCID 178418306, compound

Product 1

HCID 229340406-methyl-1H-indazole-5-carboxylic acid

Procedure

This compound was prepared in a manner similar to that shown in Scheme 3, using 5-bromo-6-methyl-1H-indazole as the starting material, which was prepared in a manner similar to that of 5-bromo-6-fluoro-1H-indazole. The starting material was treated with t-butyl lithium and carbon dioxide to yield 6-methyl-1H-indazole-5-carboxylic acid, which was in turn treated with thiosemicarbazide and polyphosphoric acid to form 94.

Workup

  1. customThis compound was prepared in a manner similar to

Sources & evidence

ORD record
ord-505e80425b7145f6bdeb30a6f2056831
Source dataset
uspto-grants-2010_04
Patent number
US07700636B2

Reaction notes

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