Iodine → HCID 178519380, compound

HRID 1521773Notes

Reaction equation

HRID 1521773 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH:10]=[O:11])=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[OH-].[Na+].[I:14]I>O1CCOCC1.O>[I:14][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[C:6]([CH:10]=[O:11])[CH:5]=2)[NH:1][N:2]=1

Participants

6

Reactant 3

HCID 807Iodine2×HCID 14798Sodium HydroxideHCID 212506441H-Indazole-5-carboxaldehyde2×

Product 1

HCID 178519380HCID 178519380, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

20 g (137 mmol) 1H-indazole-5-carbaldehyde [preparation described in US 2005/0227968-A1 (Intermediate 1)], dissolved in 1,4-dioxane (640 ml), were treated with a solution of sodium hydroxide (82 g, 2053 mmol) in water (640 ml). Then, 43.2 g (170 mmol) iodine were added, and the mixture was stirred at room temperature for 1 h. Subsequently, a second batch of 43.2 g (170 mmol) iodine was added, and the mixture was again stirred at room temperature for 1 h. The mixture was concentrated under reduced pressure yielding a solid precipitate. After filtration, the precipitate was washed with water and dried under high vacuum over phosphorous oxide in a desiccator for 12 h affording the title compound (26.6 g, 72% of th.) as a pale yellow solid.

Workup

  1. stirringthe mixture was again stirred at room temperature for 1 h
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customyielding a solid precipitate
  4. filtrationAfter filtration
  5. washthe precipitate was washed with water
  6. dry with materialdried under high vacuum over phosphorous oxide in a desiccator for 12 h

Sources & evidence

ORD record
ord-c579979d45614f87a29bcafb10f88dc1
Source dataset
uspto-grants-2015_07
Patent number
US09073939B2

Reaction notes

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