6-(4-hydroxytetrahydropyran-4-yl)-1H-indazole-3-carboxylic acid tert-butyl ester → 6-(3,6-dihydro-2H-pyran-4-yl)-1H-indazole-3-carboxylic acid

HRID 747103Notes

Reaction equation

HRID 747103 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>FC(F)(F)C(O)=O>[O:20]1[CH2:19][CH:18]=[C: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)[CH2:22][CH2:21]1

Participants

3

Reactant 1

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

Product 1

HCID 667026626-(3,6-dihydro-2H-pyran-4-yl)-1H-indazole-3-carboxylic acidYield 76%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

6-(4-Hydroxytetrahydropyran-4-yl)-1H-indazole-3-carboxylic acid tert-butyl ester (0.86 mmol) was dissolved in trifluoroacetic acid (3 mL) and the mixture was maintained at room temperature for 16 h. The solvent was removed in vacuo and the residue was triturated with ethyl acetate to provide 6-(3,6-dihydro-2H-pyran-4-yl)-1H-indazole-3-carboxylic acid (76%). The acid was coupled with the bicyclobase according to procedure A.

Workup

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

Sources & evidence

ORD record
ord-3ddeb57022b845d586193107016f294d
Source dataset
uspto-grants-2008_07
Patent number
US07396833B2

Reaction notes

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