Hydrogen Peroxide → 3-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-5-carboxamide

HRID 1273034Notes

Reaction equation

HRID 1273034 reaction equation
[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]#[N:12])[CH:9]=2)[N:4]([CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][O:14]2)[N:3]=1.[OH:19]O.[OH-].[Na+]>C(O)C>[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([NH2:12])=[O:19])[CH:9]=2)[N:4]([CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][O:14]2)[N:3]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 224799453-Bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-5-carbonitrile

Product 1

HCID 224799153-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-5-carboxamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

The title compound was prepared by adding the 3-bromo-1-perhydro-2H-pyran-2-yl-1H-indazole-5-carbonitrile (15.20 g, 49.65 mmol), ethanol (130 mL), 30% hydrogen peroxide (aqueous) (130 mL), and 6 N sodium hydroxide (aqueous) (9 mL) to a 2 liter round bottom flask. This mixture was heated at 50° C. for 1 hour, and removed from the heat to allow to cool to room temperature. The pH was adjusted to ˜3 by adding 6 N hydrochloride solution (aqueous) resulting in a precipitate. This precipitate was filtered and washed with water (15.13 g, 94%): ES-MS (m/z) 324 [M+1]+.

Workup

  1. customremoved from the
  2. temperatureheat
  3. temperatureto cool to room temperature
  4. additionby adding 6 N hydrochloride solution (aqueous)
  5. customresulting in a precipitate
  6. filtrationThis precipitate was filtered
  7. washwashed with water (15.13 g, 94%)

Sources & evidence

ORD record
ord-a95cde5ea3e645f0bb95a9c7ee242ece
Source dataset
uspto-grants-2007_04
Patent number
US07208513B2

Reaction notes

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