Sodium Carbonate → 1-(2-chloro-phenyl)-5-(4'-(methylsulfanyl)-biphenyl-4-yl)-3-pentafluoroethyl-4,5-dihydro-1H-pyrazole

HRID 2207955Notes

Reaction equation

HRID 2207955 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:19])[N:11]=[C:10]([C:20]([F:26])([F:25])[C:21]([F:24])([F:23])[F:22])[CH2:9]2)=[CH:4][CH:3]=1.[CH3:27][S:28][C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[N:12]1[CH:8]([C:5]2[CH:6]=[CH:7][C:2]([C:32]3[CH:33]=[CH:34][C:29]([S:28][CH3:27])=[CH:30][CH:31]=3)=[CH:3][CH:4]=2)[CH2:9][C:10]([C:20]([F:25])([F:26])[C:21]([F:22])([F:24])[F:23])=[N:11]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27339594-(Methylthio)phenylboronic acidHCID 1184316755-(4-bromo-phenyl)-1-(2-chloro-phenyl)-3-pentafluoroethyl-4,5-dihydro-1H-pyrazole

Product 1

HCID 1184319271-(2-chloro-phenyl)-5-(4'-(methylsulfanyl)-biphenyl-4-yl)-3-pentafluoroethyl-4,5-dihydro-1H-pyrazoleYield 58.8%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 5-(4-bromo-phenyl)-1-(2-chloro-phenyl)-3-pentafluoroethyl-4,5-dihydro-1H-pyrazole (100.0 mg, 0.19 mmol) prepared in Step 3 of Preparation 1, 4-(methylthio)phenylboronic acid (80.0 mg, 0.28 mmol), Pd(PPh3)4 (26 mg, cat.), and a 2N sodium carbonate solution 0.6 mL in N,N-dimethylformamide (5 mL) were stirred at 80° C. for 6 hours. The reaction mixture was concentrated under reduced pressure and then extracted with ethyl acetate. The extract was washed with distilled water, dried on anhydrous magnesium sulfate, and then concentrated under reduced pressure to give a yellow liquid residue. The resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/20) to give 55.5 mg of the titled compound as a pale yellow liquid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with distilled water
  4. dry with materialdried on anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give a yellow liquid residue
  7. customThe resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/20)

Sources & evidence

ORD record
ord-6170f53e1d464c05947602287bfda6e0
Source dataset
uspto-grants-2016_06
Patent number
US09376420B2

Reaction notes

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