1,3-Dibromopropane → 1-(3-Bromo-propyl)-1H-indazole

HRID 1168843Notes

Reaction equation

HRID 1168843 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4]Br.[NH:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[N:7]1.[OH-].[K+].C(OCC)(=O)C>CN(C=O)C.O>[Br:1][CH2:2][CH2:3][CH2:4][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[N:7]1

Participants

7

Reactant 4

HCID 80011,3-DibromopropaneHCID 8857Ethyl AcetateHCID 92211H-IndazoleHCID 14797Potassium Hydroxide

Product 1

HCID 112649241-(3-Bromo-propyl)-1H-indazoleYield 62.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1,3-Dibromopropane (508 μl, 5.0 mmol)) was dissolved in 10 mL DMF and placed in a 100 mL flask. Indazole (592 mg, 5.0 mmol) and KOH (282 mg, 5.0 mmol) were added and the suspension was stirred overnight at room temperature. Ethyl acetate (50 mL) and water (50 mL) were added. Phases were separated and the aqueous phase was re-extracted with ethyl acetate (50 mL). The combined organic phases were washed with brine, dried over magnesium sulphate and evaporated to dryness to produce 751 mg of a yellow oil. Crude product was further purified by column chromatography (0-10% methanol:dichloromethane) to produce pure 22 (169 mg, 14%).

Workup

  1. customplaced in a 100 mL flask
  2. customPhases were separated
  3. extractionthe aqueous phase was re-extracted with ethyl acetate (50 mL)
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over magnesium sulphate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-fb7fa55680304480b82491c82a7cb597
Source dataset
uspto-grants-2003_09
Patent number
US06627645B2

Reaction notes

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