Sodium Carbonate → HCID 118431709, compound

HRID 2207988Notes

Reaction equation

HRID 2207988 reaction equation
Br[C:2]1[CH:3]=[C:4]([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:5]=[CH:6][CH:7]=1.[C:27]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1B(O)O)(=[O:29])[CH3:28].C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].CN(C)C=O>[C:27]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([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:25])([F:26])[C:21]([F:22])([F:23])[F:24])[CH2:9]2)[CH:3]=1)(=[O:29])[CH3:28]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343092-Acetylphenylboronic acidHCID 118431639HCID 118431639, compound

Product 1

HCID 118431709HCID 118431709, compoundYield 50.7%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

5-(3-Bromo-phenyl)-1-(2-chloro-phenyl)-3-pentafluoroethyl-4,5-dihydro-1H-pyrazole (20.0 mg, 0.04 mmol) prepared in Step 1 of Preparation 6, 2-acetylphenylboronic acid (9.0 mg, 0.06 mmol), Pd(dppf)Cl2 (2.0 mg, cat.) and a 2N sodium carbonate solution (0.5 mL) were added to N,N-dimethylformamide (0.5 mL). The reaction mixture was stirred at 80° C. for 2 hours and then filtered through celite pad. A saturated solution of ammonium chloride was added to the filtrate, which was then extracted with ethyl acetate three times. The combined extract was washed with brine, 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=1/5) to give 10.0 mg of the titled compound as a yellow liquid.

Workup

  1. filtrationfiltered through celite pad
  2. additionA saturated solution of ammonium chloride was added to the filtrate, which
  3. extractionwas then extracted with ethyl acetate three times
  4. extractionThe combined extract
  5. washwas washed with brine
  6. dry with materialdried on anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto give a yellow liquid residue
  9. customThe resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/5)

Sources & evidence

ORD record
ord-b4f109b8e960480f81bda3abc8299493
Source dataset
uspto-grants-2016_06
Patent number
US09376420B2

Reaction notes

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