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

HRID 2362855Notes

Reaction equation

HRID 2362855 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 taken up 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-565dacba5c904e04ad7732e28e653a15
Source dataset
uspto-grants-2014_04
Patent number
US08691841B2

Reaction notes

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