Sodium Hydroxide → HCID 68614934, compound

HRID 902550Notes

Reaction equation

HRID 902550 reaction equation
[Br:1][C:2]1[C:10]2[C:6](=[CH:7][N:8]([CH3:11])[N:9]=2)[CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:15])(=O)=O.[OH-].[Na+]>C(O)(=O)C>[Br:1][C:2]1[C:10]2[C:6](=[C:7]([Cl:15])[N:8]([CH3:11])[N:9]=2)[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24648Sulfuryl chlorideHCID 210945807-bromo-2-methyl-2H-indazole

Product 1

HCID 68614934HCID 68614934, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 7-bromo-2-methyl-2H-indazole (6: R=Me; 0.500 g, 2.37 mmol) in 5 mL of acetic acid was added sulfuryl chloride (0.29 mL, 3.6 mmol). The mixture was stirred for 5 h, then 30 mL of a 2 M aqueous NaOH solution were added. The mixture was extracted with three 30 mL portions of ethyl acetate, and the combined organic layers were dried over Na2SO4, filtered, and concentrated to a white solid. Column chromatography (0→15% EtOAc/hexanes) afforded slightly impure 7-bromo-3-chloro-2-methyl-2H-indazole (25: R=Me; 0.530 g; 90%) that was used without further purification.

Workup

  1. extractionThe mixture was extracted with three 30 mL portions of ethyl acetate
  2. dry with materialthe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated to a white solid

Sources & evidence

ORD record
ord-0f74da9cf4b04939a0f5a3ee44e6d989
Source dataset
uspto-grants-2008_04
Patent number
US07365211B2

Reaction notes

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