Dichloromethane → 6-(tetrahydropyran-4-yl)-1H-indazole-3-carboxylic acid

HRID 1864614Notes

Reaction equation

HRID 1864614 reaction equation
C([O:5][C:6]([C:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]3(O)[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[CH:14][CH:15]=2)[NH:10][N:9]=1)=[O:7])(C)(C)C.C([SiH](CC)CC)C.ClCCl>FC(F)(F)C(O)=O>[O:20]1[CH2:21][CH2:22][CH:17]([C:13]2[CH:12]=[C:11]3[C:16]([C:8]([C:6]([OH:7])=[O:5])=[N:9][NH:10]3)=[CH:15][CH:14]=2)[CH2:18][CH2:19]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 12052TriethylsilaneHCID 667025586-(4-hydroxytetrahydropyran-4-yl)-1H-indazole-3-carboxylic acid tert-butyl ester

Product 1

HCID 667025916-(tetrahydropyran-4-yl)-1H-indazole-3-carboxylic acidYield 60%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

6-(4-Hydroxytetrahydropyran-4-yl)-1H-indazole-3-carboxylic acid tert-butyl ester (1.0 mmol) was dissolved in trifluoroacetic acid (5 mL), triethylsilane (2 mL), and dichloromethane (3 mL) and the mixture was refluxed for 16 h. The solvent was removed in vacuo and the residue was triturated with ethyl acetate to provide 6-(tetrahydropyran-4-yl)-1H-indazole-3-carboxylic acid (60%) as a tan solid.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was triturated with ethyl acetate

Sources & evidence

ORD record
ord-3e7b56185a7d492d98e22757c9623f87
Source dataset
uspto-grants-2009_12
Patent number
US07625924B2

Reaction notes

Loading…