Water → HCID 21912705, compound
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
Product 1
Reagents, catalysts & solvents 1
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 the title compound as a viscous oil.
Workup
- customthe reaction was quenched with aq. sodium bicarbonate
- customThe mixture was partitioned between ethyl acetate and aq. sodium bicarbonate
- extractionThe aqueous layer was extracted with ethyl acetate (3×)
- washThe combined organic phase was washed with brine
- dry with materialdried over anhydrous magnesium sulfate
- customPurification by flash chromatography (hexanes
Sources & evidence
- ORD record
- ord-0b6da2ce7b584060b3754952d30d708e
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07125887B2
Reaction notes
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