Water → HCID 19737191, compound

HRID 258254Notes

Reaction equation

HRID 258254 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[C:21]2[C:16](=[CH:17][C:18]([N+:23]([O-:25])=[O:24])=[C:19]([OH:22])[CH:20]=2)[CH:15]=[N:14]1.[H-].[Na+].[CH2:28](Br)[C:29]#[CH:30].O>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:9])[F:10])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[C:21]2[C:16](=[CH:17][C:18]([N+:23]([O-:25])=[O:24])=[C:19]([O:22][CH2:30][C:29]#[CH:28])[CH:20]=2)[CH:15]=[N:14]1

Participants

6

Reactant 4

HCID 962WaterHCID 7842Propargyl bromideHCID 24758Sodium hydrideHCID 135749813HCID 135749813, compound

Product 1

HCID 19737191HCID 19737191, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(2,6-dichloro-4-trifluoromethylphenyl)-6-hydroxy-5-nitroindazole [Compound No. 31] (3 g) in N,N-dimethylformamide, 60% sodium hydride (0.5 g) was added, and the resultant mixture was stirred while cooling with ice. After 10 minutes, propargyl bromide (1.2 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 diethyl ether. 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-(2,6-dichloro-4-trifluoromethylphenyl)-5-nitro-6-propargyloxyindazole (2.8 g).

Workup

  1. temperaturewhile cooling with ice
  2. customAfter completion of the reaction
  3. extractionextracted with diethyl ether
  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-c18b76a205d3456c81e976ffb8628338
Source dataset
uspto-grants-1993_11
Patent number
US05266556

Reaction notes

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