Water → tert-Butyl 3-difluoromethoxy-6-hydroxyindazole-1-carboxylate

HRID 1873965Notes

Reaction equation

HRID 1873965 reaction equation
C([O:8][C:9]1[CH:17]=[C:16]2[C:12]([C:13]([O:25][CH:26]([F:28])[F:27])=[N:14][N:15]2[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[CH:11][CH:10]=1)C1C=CC=CC=1.O.[H][H]>[Pd].C1COCC1>[F:28][CH:26]([F:27])[O:25][C:13]1[C:12]2[C:16](=[CH:17][C:9]([OH:8])=[CH:10][CH:11]=2)[N:15]([C:18]([O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:19])[N:14]=1

Participants

6

Reactant 3

HCID 962WaterHCID 45280135tert-Butyl 6-(benzyloxy)-3-difluoromethoxyindazole-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 135869961tert-Butyl 3-difluoromethoxy-6-hydroxyindazole-1-carboxylateYield 97.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Tert-butyl 6-(benzyloxy)-3-(difluoromethoxy)-indazole-1-carboxylate (262.5 mg) which can be prepared according to the method described in Reference example 33, etc. and 5% palladium on carbon-STD-type-50% wet with water (109.9 mg; manufactured by N. E. Chemcat Corp.) were suspended in dehydrated THF (3.4 mL; manufactured by Kanto Chemical Co., Inc.). After replacing the reaction system with hydrogen, it was stirred overnight at room temperature. After replacing the reaction solution with nitrogen, the mixture was filtered and the filtrate was concentrated under reduced pressure to obtain the title compound (197.2 mg).

Workup

  1. filtrationthe mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b65163548ca1448b8e664a85980b1705
Source dataset
uspto-grants-2012_11
Patent number
US08304443B2

Reaction notes

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