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

HRID 706658

Reaction equation

HRID 706658 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=O)C.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) in dry DMF (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 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. stirringThe mixture was stirred at ambient temperature for 3 days
  2. extractionextracted into ethyl acetate
  3. washwashed with saturated sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting material was purified
  8. washeluting with hexane/ethyl acetate (3:1)

Sources & evidence

ORD record
ord-bfc3d35281fe42a88e22bffc9552352b
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Linked notes

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