Dimethylformamide → 4-Chloro-1-(5-trifluoromethyl-2-pyridyl) indazole N-Oxide

HRID 1003159Notes

Reaction equation

HRID 1003159 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][N+:3]=1[O-].[Cl:13][C:14]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:15]=1[CH:16]=[N:17][NH:18]2.C(=O)([O-])[O-:24].[K+].[K+].CN(C)C=O>[Cl-].[Na+].O>[Cl:13][C:14]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:15]=1[CH:16]=[N:17][N+:18]2([O-:24])[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 3930374-Chloro-1H-indazoleHCID 154483422-Chloro-5-(trifluoromethyl)pyridine 1-oxide

Product 1

HCID 867552754-Chloro-1-(5-trifluoromethyl-2-pyridyl) indazole N-OxideYield 73%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2-chloro-5-trifluoromethylpyridine N-Oxide (1.8 g, 0.009 mol), 4-chloroindazole (1.1 g, 0.007 mol), anhydrous potassium carbonate (1.5 g, 0.0105 mol) and dimethylformamide (20 ml) was stirred and warmed to 70° C. Within 1 hour the reaction was complete based on thin-layer chromatographic analysis. The solution was poured into brine (300 ml) and the precipitate was collected by suction filtration and was washed with water until the filtrate was clear. The brick-red solid was air dried to yield 1.6 g (73%) of the desired product, m.p. 154° C. (dec).

Workup

  1. filtrationthe precipitate was collected by suction filtration
  2. washwas washed with water until the filtrate
  3. customdried

Sources & evidence

ORD record
ord-6d746c0159184ce5b3ffeb1e4d5b6e07
Source dataset
uspto-grants-2000_04
Patent number
US06046136

Reaction notes

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