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

HRID 1867274Notes

Reaction equation

HRID 1867274 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-3e96ddb0bf3d41ee8ba26d1a5636830f
Source dataset
uspto-grants-2009_12
Patent number
US07632831B2

Reaction notes

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