Dimethylformamide → HCID 89666806, compound

HRID 2171216Notes

Reaction equation

HRID 2171216 reaction equation
[CH3:1][O:2][C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[NH:5][N:4]=1.Br[CH2:16][CH2:17][O:18][CH3:19].CN(C=O)C.[H-].[Na+]>CCCC[N+](CCCC)(CCCC)CCCC.[I-].O>[CH3:1][O:2][C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[N:5]([CH2:16][CH2:17][O:18][CH3:19])[N:4]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 72207560HCID 72207560, compound

Product 1

HCID 89666806HCID 89666806, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

3-Methoxy-5-nitro-1H-indazole (97 mg), 1-bromo-2-methoxyethane (70 μl, and TBAI (2 mg) were added to a DMF (1 ml) suspension containing sodium hydride (60% in oil) (24 mg) under ice cooling, followed by stirring at 100° C. for 1 hour. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layers were washed with water and saturated saline and dried over anhydrous sodium sulfate. Then, the solvent was distilled away under reduced pressure, and the obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=1:0 to 1:1). A 3-methoxy-1-(2-methoxyethyl)-5-nitro-1H-indazole (50 mg) was thus obtained.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layers were washed with water and saturated saline
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThen, the solvent was distilled away under reduced pressure
  5. customthe obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=1:0 to 1:1)

Sources & evidence

ORD record
ord-b9fb69d30fba4eea9da58af908d7bc33
Source dataset
uspto-grants-2015_06
Patent number
US09051310B2

Reaction notes

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