Ethanol → HCID 118432017, compound

HRID 2207961Notes

Reaction equation

HRID 2207961 reaction equation
Br[C:2]1[CH:3]=[N:4][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:6][CH:7]=1.[C:27]([C:30]1[CH:31]=[C:32](B(O)O)[CH:33]=[CH:34][CH:35]=1)(=[O:29])[CH3:28].C(=O)([O-])[O-].[Na+].[Na+].C(O)C>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.C1(C)C=CC=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:34]3[CH:33]=[CH:32][CH:31]=[C:30]([C:27](=[O:29])[CH3:28])[CH:35]=3)=[CH:3][N:4]=2)[CH2:9][C:10]([C:20]([F:26])([F:25])[C:21]([F:24])([F:23])[F:22])=[N:11]1

Participants

7

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 27343103-Acetylphenylboronic acidHCID 118431784HCID 118431784, compound

Product 1

HCID 118432017HCID 118432017, compoundYield 20.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

5-(3-Bromo-pyridin-6-yl)-1-(2-chloro-phenyl)-3-pentafluoroethyl-4,5-dihydro-1H-pyrazole (20.0 mg, 0.04 mmol) prepared in Step 4 of Preparation 3, 3-acetylphenylboronic acid (11.0 mg, 0.07 mmol), Pd(PPh3)4 (2.0 mg, cat.) and a 2N sodium carbonate solution (210.0 uL) were added to a mixed solvent of ethanol (210.0 uL) and toluene (310.0 uL). The reaction mixture was stirred at 80° C. for 1 hour 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=1/6) to give 4.0 mg of the titled compound as a white 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=1/6)

Sources & evidence

ORD record
ord-86566233b8c64fd2afceb28dfcae8beb
Source dataset
uspto-grants-2016_06
Patent number
US09376420B2

Reaction notes

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