Iodoethane → 5-Bromo-1-ethyl-1H-indazole

HRID 1403355Notes

Reaction equation

HRID 1403355 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[CH:5]2.[H-].[Na+].I[CH2:14][CH3:15]>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:14][CH3:15])[N:6]=[CH:5]2

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 7619295-bromo-1H-indazole

Product 1

HCID 225589325-Bromo-1-ethyl-1H-indazoleYield 52.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-bromo-1H-indazole (1 g, 5.10 mmol) in tetrahydrofuran (30 mL) was added sodium hydride (330 mg, 8.25 mmol) at 0° C. with stirring for 30 min, iodoethane (1.72 g, 11.04 mmol) was added dropwise. The reaction mixture was stirred overnight at room temperature. The reaction was then quenched with water (50 mL), extracted with ethyl acetate (3×80 mL) and the organic layers combined, dried over anhydrous magnesium sulfate and concentrated under vacuum to give the residue, which was purified by a silica gel column with 1% to 5% ethyl acetate in petroleum ether to afford 5-bromo-1-ethyl-1H-indazole as yellow oil (598 mg, 52%).

Workup

  1. stirringThe reaction mixture was stirred overnight at room temperature
  2. customThe reaction was then quenched with water (50 mL)
  3. extractionextracted with ethyl acetate (3×80 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under vacuum
  6. customto give the residue, which
  7. customwas purified by a silica gel column with 1% to 5% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-1a73738ea54344cca769a274ba2a36b0
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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