Butane → HCID 118431887, compound

HRID 2207973Notes

Reaction equation

HRID 2207973 reaction equation
Br[C:2]1[CH:7]=[C:6]([F:8])[C:5]([S:9]([CH3:12])(=[O:11])=[O:10])=[CH:4][C:3]=1[F:13].CCCC.[F:18][C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=1[N:26]1[CH:30]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33](B3OC(C)(C)C(C)(C)O3)[CH:32]=2)[CH2:29][C:28]([C:46]([F:52])([F:51])[C:47]([F:50])([F:49])[F:48])=[N:27]1.C(=O)([O-])[O-].[Na+].[Na+]>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.O.C(O)C>[F:13][C:3]1[CH:4]=[C:5]([S:9]([CH3:12])(=[O:11])=[O:10])[C:6]([F:8])=[CH:7][C:2]=1[C:33]1[CH:34]=[CH:35][CH:36]=[C:31]([CH:30]2[N:26]([C:20]3[CH:21]=[CH:22][C:23]([F:25])=[CH:24][C:19]=3[F:18])[N:27]=[C:28]([C:46]([F:52])([F:51])[C:47]([F:48])([F:50])[F:49])[CH2:29]2)[CH:32]=1

Participants

8

Reactant 4

HCID 7843ButaneHCID 10340Sodium CarbonateHCID 118432096HCID 118432096, compoundHCID 131735963HCID 131735963, compound

Product 1

HCID 118431887HCID 118431887, compoundYield 25.2%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
88 °C

Procedure

To 1-bromo-2,5-difluoro-4-(methylsulfonyl)benzene (19.0 mg, 0.07 mmol), were added 1,2-dimethylethane (1.5 mL) and Pd(PPh3)4 (8.1 mg, cat.). To the reaction mixture, were added 1-(2,4-difluoro-phenyl)-3-pentafluoroethyl-5-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-4,5-dihydro-1H-pyrazole (35 mg, 0.07 mmol) prepared in Step 1, ethanol (350.0 uL), and a 2N sodium carbonate solution (350.0 uL). The reaction mixture was stirred at 88° C. for 2 hours. Distilled water was added to the reaction mixture, which was then extracted with diethyl ether two 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 pale yellow liquid.

Workup

  1. extractionwas then extracted with diethyl ether two times
  2. extractionThe combined extract
  3. washwas washed with brine
  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=1/5)

Sources & evidence

ORD record
ord-564af7d37ed14fac8325fd0cf10ae4fa
Source dataset
uspto-grants-2016_06
Patent number
US09376420B2

Reaction notes

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