Potassium Carbonate → HCID 59631861, compound

HRID 2369026Notes

Reaction equation

HRID 2369026 reaction equation
Br[C:2]1[S:6][C:5]([C:7]2[CH:11]=[CH:10][N:9]([CH3:12])[N:8]=2)=[CH:4][CH:3]=1.[CH3:13][S:14]([C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[CH:21][CH:22]=1)(=[O:16])=[O:15].C([O-])([O-])=O.[K+].[K+]>>[CH3:13][S:14]([C:17]1[CH:22]=[C:21]([C:2]2[S:6][C:5]([C:7]3[CH:11]=[CH:10][N:9]([CH3:12])[N:8]=3)=[CH:4][CH:3]=2)[CH:20]=[CH:19][CH:18]=1)(=[O:16])=[O:15]

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 27735423-(Methylsulfonyl)phenylboronic acidHCID 59633050HCID 59633050, compound

Product 1

HCID 59631861HCID 59631861, compoundYield 42%

Conditions

Temperature
85 °C

Procedure

A stirred mixture of 3-(5-bromothiophen-2-yl)-1-methyl-1H-pyrazole (0.20 g, 0.83 mmol), 3-methanesulfonyl-phenylboronic acid (0.20 g, 1.0 mmol), K2CO3 (345 mg, 2.5 mmol), Cl2Pd(dppf).DCM (82 mg, 10 mol %) and H2O (0.6 mL) in dioxane (6 mL) was sparged with Argon for 5 min and then heated at 85° C. as a sealed flask. After 6 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/DCM, 2:98 to 5:95) to give the title compound (0.11 g, 42%) as a white solid. 1H-NMR (CD2Cl2): δ 8.15 (1H, m), 7.89 (1H, m), 7.80 (1H, m), 7.60 (1H, m), 7.40 (2H, m), 7.29 (1H, d), 6.50 (1H, d), 3.91 (3H, s), 3.07 (3H, s).

Workup

  1. customDCM (82 mg, 10 mol %) and H2O (0.6 mL) in dioxane (6 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/DCM, 2:98 to 5:95)

Sources & evidence

ORD record
ord-ca78273ee5ef4c3dba68b2b7820ac7f6
Source dataset
uspto-grants-2014_04
Patent number
US08703805B2

Reaction notes

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