Methanol → 3-methoxy-1-((6-methylpyridin-3-yl)methyl)-4-nitro-1H-indazole

HRID 79467Notes

Reaction equation

HRID 79467 reaction equation
I[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]([CH2:14][C:15]2[CH:16]=[N:17][C:18]([CH3:21])=[CH:19][CH:20]=2)[N:3]=1.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.[F-].[K+].[CH3:38][OH:39]>C1(C)C=CC=CC=1.[Cu](I)I>[CH3:38][O:39][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]([CH2:14][C:15]2[CH:16]=[N:17][C:18]([CH3:21])=[CH:19][CH:20]=2)[N:3]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 13181,10-PhenanthrolineHCID 522689Potassium FluorideHCID 672608103-iodo-1-((6-methylpyridin-3-yl)methyl)-4-nitro-1H-indazole

Product 1

HCID 672596893-methoxy-1-((6-methylpyridin-3-yl)methyl)-4-nitro-1H-indazoleYield 66%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 3-iodo-1-((6-methylpyridin-3-yl)methyl)-4-nitro-1H-indazole (0.520 g, 1.32 mmol), 1,10-phenanthroline (0.238 g, 1.32 mmol), copper iodide (0.251 g, 1.32 mmol) and potassium fluoride (40% on alumina) (1.05 g, 7.26 mmol) in methanol (2.7 mL) and toluene (13 mL) was purged with argon and heated at reflux for 14 hours. After cooling, the mixture was filtered through glass fiber filter paper, concentrated under reduced pressure and purified by silica gel chromatography (5-25% EtOAc in hexanes) to give 3-methoxy-1-((6-methylpyridin-3-yl)methyl)-4-nitro-1H-indazole (0.260 g, 66% yield) as a brown gum.

Workup

  1. customwas purged with argon
  2. temperatureheated
  3. temperatureat reflux for 14 hours
  4. temperatureAfter cooling
  5. filtrationthe mixture was filtered through glass fiber
  6. filtrationfilter paper
  7. concentrationconcentrated under reduced pressure
  8. custompurified by silica gel chromatography (5-25% EtOAc in hexanes)

Sources & evidence

ORD record
ord-c949dc8c7c4e42afa506852d6723aed0
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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