Water → HCID 1473929, compound

HRID 258248Notes

Reaction equation

HRID 258248 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[CH:7]2)([O-:3])=[O:2].[H-].[Na+].Cl[C:16]1[C:21]([Cl:22])=[CH:20][C:19]([C:23]([F:26])([F:25])[F:24])=[CH:18][N:17]=1.O>CN(C)C=O>[Cl:22][C:21]1[C:16]([N:9]2[C:10]3[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=3)[CH:7]=[N:8]2)=[N:17][CH:18]=[C:19]([C:23]([F:25])([F:24])[F:26])[CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 215015-NitroindazoleHCID 24758Sodium hydrideHCID 1122342,3-Dichloro-5-(trifluoromethyl)pyridine

Product 1

HCID 1473929HCID 1473929, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-nitroindazole (1.63 g) in N,N-dimethylformamide (10 ml), 60% sodium hydride (0.5 g) was added, and the resultant mixture was stirred while cooling with ice. After 10 minutes, 2,3-dichloro-5-trifluoromethylpyridine (2.1 g) was added thereto, and the resultant mixture was stirred at room temperature for 30 minutes. After completion of the reaction, the reaction mixture was poured into water and extracted with ethyl acetate. The extract was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography with hexane-ethyl acetate (4:1) to give 1-(3-chloro-5-trifluoromethylpyridin-2-yl)-5-nitroindazole (1.8 g)

Workup

  1. temperaturewhile cooling with ice
  2. customAfter completion of the reaction
  3. extractionextracted with ethyl acetate
  4. dry with materialThe extract was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography with hexane-ethyl acetate (4:1)

Sources & evidence

ORD record
ord-7ddbcfbf2ec4401ca4f511d4cf3c343b
Source dataset
uspto-grants-1993_11
Patent number
US05266556

Reaction notes

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