Water → HCID 21912705, compound

HRID 1862707Notes

Reaction equation

HRID 1862707 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-ea8a090b5a7247029ba9f9582f141deb
Source dataset
uspto-grants-2003_03
Patent number
US06538002B1

Reaction notes

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