1-(4-Bromophenyl)-4,4,4-trifluorobutane-1,3-dione → 2-[5-(4-Bromo-phenyl)-3-trifluoromethyl-pyrazol-1-yl]-5-methanesulfonyl-pyridine

HRID 1634276Notes

Reaction equation

HRID 1634276 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3](=O)[CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][CH:8]=1)=O.Cl.[NH:18]([C:20]1[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:22][N:21]=1)[NH2:19]>C(O)C>[CH3:29][S:26]([C:23]1[CH:24]=[CH:25][C:20]([N:18]2[C:5]([C:7]3[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][CH:8]=3)=[CH:4][C:3]([C:2]([F:16])([F:15])[F:1])=[N:19]2)=[N:21][CH:22]=1)(=[O:27])=[O:28]

Participants

4

Reactant 2

HCID 27714771-(4-Bromophenyl)-4,4,4-trifluorobutane-1,3-dioneHCID 222268132-Hydrazino-5-(methylsulfonyl)pyridine hydrochloride

Product 1

HCID 99114082-[5-(4-Bromo-phenyl)-3-trifluoromethyl-pyrazol-1-yl]-5-methanesulfonyl-pyridineYield 53.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4,4,4-Trifluoro-1-(4-bromophenyl)1,3-butanedione (600 mg) (prepared according to the method of Thomas D. Penning, et al.; J. Med. Chem., 1997, 40, 1347-1365.) and 2-hydrazino-5-(methylsulfonyl)pyridine hydrochloride (420 mg) were mixed in ethanol (40 mL), and the resulting solution was refluxed for 3 days. Upon cooling, white precipitates came out. The white precipitates were collected by filtration and purified by flash chromatography using 70:30 of methylene chloride and hexane to give the title compound (450 mg).

Workup

  1. temperaturethe resulting solution was refluxed for 3 days
  2. temperatureUpon cooling
  3. customwhite precipitates
  4. customThe white precipitates
  5. filtrationwere collected by filtration
  6. custompurified by flash chromatography

Sources & evidence

ORD record
ord-c4f6bfe56f594652ab342503be34808b
Source dataset
uspto-grants-2003_01
Patent number
US06506779B1

Reaction notes

Loading…