1,3-Dibromopropane → HCID 66634166, compound

HRID 1750115Notes

Reaction equation

HRID 1750115 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([OH:10])[CH:8]=2)[CH:3]=[N:2]1.[Br:11][CH2:12][CH2:13][CH2:14]Br.C([O-])([O-])=O.[K+].[K+]>CCO>[Br:11][CH2:12][CH2:13][CH2:14][O:10][C:7]1[CH:8]=[C:9]2[C:4]([CH:3]=[N:2][NH:1]2)=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 1354839876-hydroxy-1H-indazole

Product 1

HCID 66634166HCID 66634166, compoundYield 7.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1H-indazol-6-ol (600 mg, 4.5 mmol), 1,3-dibromopropane (1.4 mL, 13.4 mmol) and anhydrous K2CO3 (618 mg, 4.5 mmol) in EtOH (20 mL) was heated to reflux and stirred overnight. Filtration gave a yellow solid which was purified by column chromatography (elution with PE/EtOAc=3:1) to afford 6-(3-bromopropoxy)-1H-indazole (intermediate 44) (84 mg, 7%) as a yellow oil.

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. filtrationFiltration
  4. customgave a yellow solid which
  5. customwas purified by column chromatography (elution with PE/EtOAc=3:1)

Sources & evidence

ORD record
ord-df0c33c417ee407590e3a48f24c2c4cb
Source dataset
uspto-grants-2015_10
Patent number
US09156822B2

Reaction notes

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