Acetic Anhydride → Methyl 5-(trifluoromethyl)-1H-indazole-7-carboxylate

HRID 2203152Notes

Reaction equation

HRID 2203152 reaction equation
[NH2:1][C:2]1[C:11]([CH3:12])=[CH:10][C:9]([C:13]([F:16])([F:15])[F:14])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(OC(=O)C)(=O)C.C([O-])(=O)C.[K+].[N:29](OCCC(C)C)=O>C(Cl)(Cl)Cl>[F:16][C:13]([F:14])([F:15])[C:9]1[CH:10]=[C:11]2[C:2](=[C:3]([C:4]([O:6][CH3:7])=[O:5])[CH:8]=1)[NH:1][N:29]=[CH:12]2

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8053Isoamyl NitriteHCID 517044Potassium AcetateHCID 118251663Methyl 2-amino-3-methyl-5-(trifluoromethyl)benzoate

Product 1

HCID 118251578Methyl 5-(trifluoromethyl)-1H-indazole-7-carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of compound 3, at 0° C. and under nitrogen atmosphere, in chloroform (0.3M) was added acetic anhydride (2.3 equiv.) drop wise and the resulting mixture was stirred for 1 h at r.t. Then potassium acetate (0.2 equiv.) was added followed by addition of isoamyl nitrite (2.2 equiv.) and the resulting mixture was heated at reflux for 16 h. After, the reaction was cooled down to r.t. While cooling, a solid precipitation was observed. The solid was filtrated and dried under vacuum to give the title compound 4. (0.324 g, 75%).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 16 h
  3. temperatureAfter, the reaction was cooled down to r.t
  4. temperatureWhile cooling
  5. customa solid precipitation
  6. filtrationThe solid was filtrated
  7. customdried under vacuum

Sources & evidence

ORD record
ord-d6c86550ca0542cba895e693e06802bb
Source dataset
uspto-grants-2016_06
Patent number
US09365569B2

Reaction notes

Loading…