Potassium Hydroxide → 3-Bromo-1-((6-methylpyridin-2-yl)methyl)-4-nitro-1H-indazole

HRID 79400

Reaction equation

HRID 79400 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[N:7][NH:8]2)([O-:3])=[O:2].[Br:13]N1C(=O)CCC1=O.[OH-].[K+].Cl.Cl[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[N:27]=1>CN(C=O)C>[Br:13][C:6]1[C:5]2[C:9](=[CH:10][CH:11]=[CH:12][C:4]=2[N+:1]([O-:3])=[O:2])[N:8]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[N:27]=2)[N:7]=1

Participants

6

Reactant 4

HCID 14797Potassium HydroxideHCID 180574-NitroindazoleHCID 67184N-bromobutanimideHCID 765456-Chloromethyl-2-methylpyridinium chloride

Product 1

HCID 672598643-Bromo-1-((6-methylpyridin-2-yl)methyl)-4-nitro-1H-indazoleYield 80.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Nitro-1H-indazole (1.0 g, 6.1 mmol) and N-bromosuccinimide (1.1 g, 6.4 mmol) were mixed with anhydrous DMF (10 mL) in a 20 mL vial. The reaction was stirred at ambient temperature for 5 minutes. KOH (1.1 g, 18.3 mmol) and 2-(chloromethyl)-6-methylpyridine hydrochloride (1.4 g, 7.6 mmol) were added to the vial and the reaction mixture was stirred for 18 hours. The product was precipitated from solution by addition of H2O (10 mL) to the reaction mixture. The solids were collected vacuum filtration, washed with H2O and dried under vacuum to afford 3-bromo-1-((6-methylpyridin-2-yl)methyl)-4-nitro-1H-indazole (1.7 g).

Workup

  1. stirringwas stirred for 18 hours
  2. customThe product was precipitated from solution by addition of H2O (10 mL) to the reaction mixture
  3. customThe solids were collected
  4. filtrationvacuum filtration
  5. washwashed with H2O
  6. customdried under vacuum

Sources & evidence

ORD record
ord-dcb6ec09e098432b8505ca359813cc51
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Linked notes

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