Carbon Dioxide → 4-methyl-1H-indazole-5-carboxylic acid

HRID 899420Notes

Reaction equation

HRID 899420 reaction equation
Br[C:2]1[C:3]([CH3:11])=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[CH:5]2.C([Li])(C)(C)C.[C:17](=[O:19])=[O:18]>>[CH3:11][C:3]1[C:2]([C:17]([OH:19])=[O:18])=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[N:6][NH:7]2

Participants

4

Reactant 3

HCID 280Carbon DioxideHCID 441192325-Bromo-4-methyl-1H-indazoleHCID 178418306HCID 178418306, compound

Product 1

HCID 229337204-methyl-1H-indazole-5-carboxylic acid

Procedure

This compound was prepared in a manner similar to the preparation of 88 using commercially available 4-bromo-2,3-dimethylaniline as starting material. After an acylation step, N-(4-bromo-2,3-dimethylphenyl)acetamide was treated with isoamyl nitrite, then 10% aqueous HCl to yield 5-bromo-4-methyl-1H-indazole. 5-bromo-4-methyl-1H-indazole was treated with t-butyl lithium and carbon dioxide to yield 4-methyl-1H-indazole-5-carboxylic acid, which in turn was treated with thiosemicarbazide and polyphorsphoric acid to form 5-(4-methyl-1H-indazol-5-yl)-1,3,4-thiadiazol-2-amine. MS (API-ES) m/z (%): 232 (100%, M++1).

Sources & evidence

ORD record
ord-0c5ac2e566e646d09821f9aa3e248095
Source dataset
uspto-grants-2008_04
Patent number
US07354944B2

Reaction notes

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