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 2390925Notes

Reaction equation

HRID 2390925 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 acids were coupled with quinuclidine amine 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-bf50a7d81af441319518d133706acd40
Source dataset
uspto-grants-2012_09
Patent number
US08273891B2

Reaction notes

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