Potassium Carbonate → HCID 59631839, compound

HRID 2369028Notes

Reaction equation

HRID 2369028 reaction equation
Br[C:2]1[C:3]([C:8]2[S:9][C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([S:19]([CH3:22])(=[O:21])=[O:20])[CH:14]=3)=[CH:11][CH:12]=2)=[N:4][N:5]([CH3:7])[CH:6]=1.[Cl:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1B(O)O.C([O-])([O-])=O.[K+].[K+]>>[Cl:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C:2]1[C:3]([C:8]2[S:9][C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([S:19]([CH3:22])(=[O:21])=[O:20])[CH:14]=3)=[CH:11][CH:12]=2)=[N:4][N:5]([CH3:7])[CH:6]=1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 27343222-Chlorophenylboronic acidHCID 59632559HCID 59632559, compound

Product 1

HCID 59631839HCID 59631839, compoundYield 67.4%

Conditions

Temperature
80 °C

Procedure

A mixture of 4-bromo-3-[5-(3-methanesulfonyl-phenyl)-thiophen-2-yl]-1-methyl-1H-pyrazole (88 mg, 022 mmol), 2-chlorophenylboronic acid (41 mg, 0.26 mmol), K2CO3 (91 mg, 0.66 mmol), Cl2Pd(dppf).DCM (18 mg, 10 mol %) and H2O (0.25 mL) in dioxane (2.5 mL) was sparged with Argon for 5 min and then heated at 80° C. as a sealed flask. After 4 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, 30:70 to 40:60) to give the title compound (64 mg, 67%). Rf 0.14 (40% EtOAc/Hex); 1H NMR (CD2Cl2): δ 8.09 (1H, m), 7.85-7.76 m), 7.60-7.49 (2H, m), 7.45 (1H, s), 7.41-7.30 (3H, m), 7.21 (1H, d), 6.70 (1H, d), 3.97 (3H, s), 3.05 (3H, s); MS (ES): 429 [M+H]+.

Workup

  1. customDCM (18 mg, 10 mol %) and H2O (0.25 mL) in dioxane (2.5 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, 30:70 to 40:60)

Sources & evidence

ORD record
ord-4b71b52ba2314f8bbf2eecd130970345
Source dataset
uspto-grants-2014_04
Patent number
US08703805B2

Reaction notes

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