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

HRID 79269

Reaction equation

HRID 79269 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.Br[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[N:17]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[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]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[N:17]=2)[N:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 125437332-(Bromomethyl)-6-methylpyridineHCID 178526562HCID 178526562, compound

Product 1

HCID 672597623-iodo-1-((6-methylpyridin-2-yl)methyl)-4-nitro-1H-indazoleYield 90.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-iodo-4-nitro-1H-indazole (172 mg, 0.596 mmol) (prepared as in Example 1, step E) in dry N,N-dimethylformamide (3 mL) under an atmosphere of dry nitrogen was added 2-(bromomethyl)-6-methylpyridine (122 mg, 0.656 mmol) and potassium carbonate (165 mg, 1.19 mmol) with magnetic stirring. The mixture was stirred at ambient temperature for 3 days. The reaction mixture was diluted with water (20 mL) and extracted into ethyl acetate. The organic phases were combined, washed with saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting material was purified using preparative chromatography on silica, eluting with hexane/ethyl acetate (3:1) to give 3-iodo-1-((6-methylpyridin-2-yl)methyl)-4-nitro-1H-indazole (213 mg).

Workup

  1. extractionextracted into ethyl acetate
  2. washwashed with saturated sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting material was purified
  7. washeluting with hexane/ethyl acetate (3:1)

Sources & evidence

ORD record
ord-a0cc15d998f44717ac7809e89779781a
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Linked notes

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