Potassium Carbonate → HCID 118431773, compound

HRID 2208071Notes

Reaction equation

HRID 2208071 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]([C:26]([F:29])([F:28])[F:27])([C:22]([F:25])([F:24])[F:23])[OH:21])[CH2:9]2)=[C:4]([F:30])[CH:3]=1.[CH3:31][S:32][C:33]1[CH:34]=[C:35](B(O)O)[CH:36]=[CH:37][CH:38]=1.C(=O)([O-])[O-].[K+].[K+]>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].O1CCOCC1>[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:37]3[CH:36]=[CH:35][CH:34]=[C:33]([S:32][CH3:31])[CH:38]=3)=[CH:3][C:4]=2[F:30])[CH2:9][C:10]([C:20]([C:26]([F:27])([F:28])[F:29])([C:22]([F:23])([F:24])[F:25])[OH:21])=[N:11]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27343833-(Methylthio)benzeneboronic acidHCID 118431851HCID 118431851, compound

Product 1

HCID 118431773HCID 118431773, compoundYield 35.5%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

5-(4-Bromo-2-fluoro-phenyl)-1-(2-chloro-phenyl)-3-[di-(trifluoromethyl)-hydroxy-methyl]-4,5-dihydro-1H-pyrazole (50.0 mg, 0.10 mmol) prepared in Step 5 of Preparation 19, 3-methylthiophenylboronic acid (17.8 mg, 0.11 mmol), potassium carbonate (40.0 mg, 0.29 mmol), and Pd(dppf)Cl2 (7.0 mg, cat.) were added to a mixed solvent of 1,4-dioxane (750.0 uL) and distilled water (150.0 uL). The reaction mixture was stirred for 15 minutes, additionally at 90° C. for 2 hours, and then ethyl acetate was added thereto. The reaction mixture was washed with distilled water and 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=1/4) to give 20.0 mg of the titled compound as a yellow liquid.

Workup

  1. distillationdistilled water (150.0 uL)
  2. additionethyl acetate was added
  3. washThe reaction mixture was washed with distilled water and 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=1/4)

Sources & evidence

ORD record
ord-9b09ef49472e401aa6fefb32cccfb152
Source dataset
uspto-grants-2016_06
Patent number
US09376420B2

Reaction notes

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