Potassium Carbonate → 3-iodo-1-((6-methylpyridin-3-yl)methyl)-4-nitro-1H-indazole

HRID 79466Notes

Reaction equation

HRID 79466 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-:13])=[O:12])[NH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:22][C:23]1[CH:24]=[CH:25][C:26]([CH3:29])=[N:27][CH:28]=1>CN(C=O)C>[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-:13])=[O:12])[N:4]([CH2:22][C:23]2[CH:28]=[N:27][C:26]([CH3:29])=[CH:25][CH:24]=2)[N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 122143395-(chloromethyl)-2-methylpyridine hydrochlorideHCID 178526562HCID 178526562, compound

Product 1

HCID 672608103-iodo-1-((6-methylpyridin-3-yl)methyl)-4-nitro-1H-indazoleYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-iodo-4-nitro-1H-indazole (3.0 g, 10.4 mmol) in DMF (25 mL) was added potassium carbonate (2.87 g, 20.8 mmol) at ambient temperature. After 15 minutes, 5-(chloromethyl)-2-methylpyridine hydrochloride (2.03 g, 11.4 mmol) was added. The mixture was allowed to stir at ambient temperature for 18 hours. The mixture was concentrated under reduced pressure and diluted with ice-water (300 mL). The precipitated solids were collected by filtration and washed with water to provide 3-iodo-1-((6-methylpyridin-3-yl)methyl)-4-nitro-1H-indazole (3.77 g, 92% yield).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additiondiluted with ice-water (300 mL)
  3. filtrationThe precipitated solids were collected by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-35057fbfc1004311b9f20fcc32bc5dc1
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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