Water → HCID 21912705, compound

HRID 1357948Notes

Reaction equation

HRID 1357948 reaction equation
[CH2:1]([N:3]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[CH:9]2)=[N:4]1)[CH3:2].[Br:12]Br.O>C(O)C>[CH2:1]([N:3]1[C:11]([Br:12])=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[CH:9]2)=[N:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 122955192-Ethylindazole

Product 1

HCID 21912705HCID 21912705, compoundYield 65.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 2-ethylindazole (2.32 g, 15.87 mmol) in ethanol (20 mL) was added bromine (2.54 g, 15.87 mmol) in ethanol (1 mL)/water (1 mL) at 0° C. After stirring at 0° C. for 10 min. and at rt for 1 h, the reaction was quenched with aq. sodium bicarbonate. The mixture was partitioned between ethyl acetate and aq. sodium bicarbonate. The aqueous layer was extracted with ethyl acetate (3×). The combined organic phase was washed with brine, and dried over anhydrous magnesium sulfate. Purification by flash chromatography (hexanes: ethyl acetate =1:1, then 100% ethyl acetate) gave 2.34 g of the title compound as a viscous oil.

Workup

  1. customthe reaction was quenched with aq. sodium bicarbonate
  2. customThe mixture was partitioned between ethyl acetate and aq. sodium bicarbonate
  3. extractionThe aqueous layer was extracted with ethyl acetate (3×)
  4. washThe combined organic phase was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customPurification by flash chromatography (hexanes

Sources & evidence

ORD record
ord-88551e2ccbe94d5aaf84b4fd23ca2858
Source dataset
uspto-grants-2003_07
Patent number
US06593346B2

Reaction notes

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