Carbon Dioxide → 6-methyl-1H-indazole-5-carboxylic acid
Reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[C:9](C)[CH:10]=1)[NH:7][N:6]=[CH:5]2.[C:12]([Li])(C)(C)C.[C:17](=[O:19])=[O:18]>>[CH3:12][C:10]1[CH:9]=[C:8]2[C:4]([CH:5]=[N:6][NH:7]2)=[CH:3][C:2]=1[C:17]([OH:19])=[O:18]Participants
4
Procedure
This compound was prepared in a manner similar to the preparation of example 88 using commercially available 4-bromo-2,5-dimethylaniline as starting material. After an acylation step, N-(4-bromo-2,6-dimethylphenyl)acetamide was treated with isoamyl nitrite, and then 10% aqueous HCl to yield 5-bromo-7-methyl-1H-indazole. 5-bromo-7-methyl-1H-indazole was treated with t-butyl lithium and carbon dioxide to yield 6-methyl-1H-indazole-5-carboxylic acid, which is in turn was treated with thiosemicarbazide and polyphosphoric acid to form 5-(7-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-67ed72276ca34528b3d92adbc22253b1
- Source dataset
- uspto-grants-2011_04
- Patent number
- US07919514B2
Reaction notes
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