1-(4-Bromophenyl)-4,4,4-trifluorobutane-1,3-dione → 5-[5-(4-bromophenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]-2-pyridinesulfonamide

HRID 965950Notes

Reaction equation

HRID 965950 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][C:10](=O)[C:11]([F:14])([F:13])[F:12])=[CH:4][CH:3]=1.Cl.[NH:18]([C:20]1[CH:21]=[CH:22][C:23]([S:26]([NH2:29])(=[O:28])=[O:27])=[N:24][CH:25]=1)[NH2:19]>C(O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:18]([C:20]3[CH:21]=[CH:22][C:23]([S:26]([NH2:29])(=[O:28])=[O:27])=[N:24][CH:25]=3)[N:19]=[C:10]([C:11]([F:14])([F:13])[F:12])[CH:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 27714771-(4-Bromophenyl)-4,4,4-trifluorobutane-1,3-dioneHCID 223138295-Hydrazino-2-pyridinesulfonamide hydrochloride

Product 1

HCID 129686175-[5-(4-bromophenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]-2-pyridinesulfonamideYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-(4-bromophenyl)-4,4,4-trifluoro-1,3-butanedione (prepared according to the method of J. Med. Chem., 1997, 40, 1347. 1.09 g, 3.71 mmol) and 5-hydrazino-2-pyridinesulfonamide hydrochloride (1.00 g, 4.45 mmol) in ethanol (50 ml) was refluxed for 18 hr. After evaporation, the obtained residue was chromatographed on a column of silica gel (200 g) eluting with ethyl acetate/hexane (1:2) to afford 1.44 g (87%) of the title compound as a white solid.

Workup

  1. customprepared
  2. customAfter evaporation
  3. customthe obtained residue was chromatographed on a column of silica gel (200 g)
  4. washeluting with ethyl acetate/hexane (1:2)

Sources & evidence

ORD record
ord-83ed859a7396470caf3139a350744ddc
Source dataset
uspto-grants-2005_10
Patent number
US06951876B2

Reaction notes

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