Potassium Carbonate → Ethyl 7-hydroxy-1-tetrahydropyran-2-YL-indazole-5-carboxylate

HRID 1880361Notes

Reaction equation

HRID 1880361 reaction equation
C([O:4][C:5]1[CH:6]=[C:7]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:8]=[C:9]2[C:13]=1[N:12]([CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][O:15]1)[N:11]=[CH:10]2)(=O)C.C([O-])([O-])=O.[K+].[K+]>CCO>[OH:4][C:5]1[CH:6]=[C:7]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:8]=[C:9]2[C:13]=1[N:12]([CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][O:15]1)[N:11]=[CH:10]2

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 66920401ethyl 7-(acetyloxy)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-5-carboxylate

Product 1

HCID 66920492Ethyl 7-hydroxy-1-tetrahydropyran-2-YL-indazole-5-carboxylateYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 7-(acetyloxy)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-5-carboxylate (6 g, 0.018 mol) was dissolved in EtOH (100 mL) and K2CO3 (7 g, 0.05 mol) was added. The reaction mixture was heated at reflux over a period of 6 hours and evaporated. The residue was treated with water (150 mL), and the product was extracted with EtOAc (3×50 mL). The combined extracts were evaporated and the residue was purified by chromatography (EtOAc/hexane, 1:4) to afford ethyl 7-hydroxy-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-5-carboxylate (4 g, 85%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux over a period of 6 hours
  3. customevaporated
  4. additionThe residue was treated with water (150 mL)
  5. extractionthe product was extracted with EtOAc (3×50 mL)
  6. customThe combined extracts were evaporated
  7. customthe residue was purified by chromatography (EtOAc/hexane, 1:4)

Sources & evidence

ORD record
ord-ed767989df1647d5bc930ca63de1a467
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

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