Potassium Acetate → 6-Bromo-1H-indazole

HRID 1477397

Reaction equation

HRID 1477397 reaction equation
F[B-](F)(F)F.[Br:6][C:7]1[CH:8]=[CH:9][C:10]([CH3:15])=[C:11]([N+:13]#[N:14])[CH:12]=1.C([O-])(=O)C.[K+]>C(Cl)(Cl)Cl.C1OCCOCCOCCOCCOCCOC1>[Br:6][C:7]1[CH:12]=[C:11]2[C:10]([CH:15]=[N:14][NH:13]2)=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 517044Potassium AcetateHCID 805030315-Bromo-2-methylbenzenediazonium tetrafluoroborate

Product 1

HCID 178424716-Bromo-1H-indazoleYield 86.7%

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 6212ChloroformSolvent

Procedure

5-Bromo-2-methylphenyldiazonium tetrafluoroborate (1.50 g) was added to a mixture of potassium acetate (1.0 g) and 18-crown-6 (70 mg) in chloroform (50 mL) at room temperature in portions and then the reaction was stirred for 2 h. The resulting mixture was filtered and washed with chloroform. The filtrate was concentrated, and the residue was dissolved in diethyl ether, which was then washed with water, brine, dried, and the solvent was removed to give the product 6-bromoindazole (0.9 g). The product was used in the next step without further purification.

Workup

  1. filtrationThe resulting mixture was filtered
  2. washwashed with chloroform
  3. concentrationThe filtrate was concentrated
  4. dissolutionthe residue was dissolved in diethyl ether
  5. washwhich was then washed with water, brine
  6. customdried
  7. customthe solvent was removed

Sources & evidence

ORD record
ord-1575ba32906f40b1908a01b86d8971e2
Source dataset
uspto-grants-2016_08
Patent number
US09403775B2

Linked notes

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