1H-Indazole-4-carboxylic acid, 1-acetyl-6-bromo-, methyl ester → methyl 6-bromo-1H-indazole-4-carboxylate

HRID 1854131Notes

Reaction equation

HRID 1854131 reaction equation
C([N:4]1[C:12]2[CH:11]=[C:10]([Br:13])[CH:9]=[C:8]([C:14]([O:16][CH3:17])=[O:15])[C:7]=2[CH:6]=[N:5]1)(=O)C>CO.Cl>[Br:13][C:10]1[CH:9]=[C:8]([C:14]([O:16][CH3:17])=[O:15])[C:7]2[CH:6]=[N:5][NH:4][C:12]=2[CH:11]=1

Participants

4

Reactant 1

HCID 682954331H-Indazole-4-carboxylic acid, 1-acetyl-6-bromo-, methyl ester

Product 1

HCID 24728062methyl 6-bromo-1H-indazole-4-carboxylateYield 71.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of methyl 1-acetyl-6-bromo-1H-indazole-4-carboxylate (18 g, 61.0 mmol) in methanol (350 mL), 6N HCl (350 mL) was added and stirred it at 60° C. for 8 h. On completion of reaction, solvent was removed under reduced pressure then basified with saturated NaHCO3 solution till pH 8. The solid precipitate was filtered and dried under vacuum before being stirred in diethyl ether for 15 min, filtered and dried to afford methyl 6-bromo-1H-indazole-4-carboxylate (11 g, 71.7%).

Workup

  1. customOn completion of reaction, solvent
  2. customwas removed under reduced pressure
  3. filtrationThe solid precipitate was filtered
  4. customdried under vacuum
  5. stirringbefore being stirred in diethyl ether for 15 min
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-ee801b3c810445cab5c8084d4be48b46
Source dataset
uspto-grants-2015_02
Patent number
US08962620B2

Reaction notes

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