Potassium Carbonate → HCID 59632604, compound

HRID 2369030Notes

Reaction equation

HRID 2369030 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:19]([F:22])([F:21])[F:20])=[CH:11][C:10]([C:23]([F:26])([F:25])[F:24])=[N:9]2)=[CH:4][CH:3]=1.[CH3:27][S:28]([C:31]1[CH:32]=[C:33](B(O)O)[CH:34]=[CH:35][CH:36]=1)(=[O:30])=[O:29].C([O-])([O-])=O.[K+].[K+]>>[CH3:27][S:28]([C:31]1[CH:36]=[C:35]([C:2]2[CH:3]=[CH:4][C:5]([N:8]3[C:12]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=4[C:19]([F:22])([F:20])[F:21])=[CH:11][C:10]([C:23]([F:25])([F:24])[F:26])=[N:9]3)=[CH:6][CH:7]=2)[CH:34]=[CH:33][CH:32]=1)(=[O:30])=[O:29]

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 27735423-(Methylsulfonyl)phenylboronic acidHCID 59632163HCID 59632163, compound

Product 1

HCID 59632604HCID 59632604, compoundYield 76.5%

Conditions

Temperature
80 °C

Procedure

A mixture of 1-(4-bromophenyl)-3-trifluoromethyl-5-(2-trifluoromethyl-phenyl)-1H-pyrazole (135 mg, 0.31 mmol), 3-methanesulfonyl-phenylboronic acid (74 mg, 0.37 mmol), K2CO3 (0.13 g, 0.93 mmol), Cl2Pd(dppf).DCM (24 mg, 10 mol %) and H2O (0.2 mL) in dioxane (2 mL) was sparged with Argon for 5 min and then heated at 80° C. as a sealed flask. After 16 h the reaction mixture was allowed to cool to ambient temperature, filtered (Celite™) and the filter agent rinsed with EtOAc. The combined filtrates were concentrated under reduced pressure and purified by chromatography (silica, EtOAc/Hex, 0:100 to 40:60) to give the title compound (121 mg, 76%). 1H NMR (DMSO-d6): δ 8.15 (m, 1H), 8.03 (d, 1H), 7.91 (m, 2H), 7.83 (d, 2H), 7.71-7.76 (m, 3H), 7.66 (m, 1H), 7.40 (d, 2H), 7.18 (s, 1H); MS(ES): 511 [M+H]+.

Workup

  1. customDCM (24 mg, 10 mol %) and H2O (0.2 mL) in dioxane (2 mL) was sparged with Argon for 5 min
  2. temperatureto cool to ambient temperature
  3. filtrationfiltered (Celite™)
  4. washthe filter agent rinsed with EtOAc
  5. concentrationThe combined filtrates were concentrated under reduced pressure
  6. custompurified by chromatography (silica, EtOAc/Hex, 0:100 to 40:60)

Sources & evidence

ORD record
ord-27a35b54b6544095aad5a9407b841d73
Source dataset
uspto-grants-2014_04
Patent number
US08703805B2

Reaction notes

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