Potassium Carbonate → HCID 59632552, compound

HRID 2369032Notes

Reaction equation

HRID 2369032 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[Cl:19])=[CH:11][C:10]([C:20]([OH:29])([C:25]([F:28])([F:27])[F:26])[C:21]([F:24])([F:23])[F:22])=[N:9]2)=[CH:4][CH:3]=1.[CH3:30][S:31]([C:34]1[CH:35]=[C:36](B(O)O)[CH:37]=[CH:38][CH:39]=1)(=[O:33])=[O:32].C([O-])([O-])=O.[K+].[K+]>>[Cl:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:12]1[N:8]([C:5]2[CH:4]=[CH:3][C:2]([C:38]3[CH:37]=[CH:36][CH:35]=[C:34]([S:31]([CH3:30])(=[O:33])=[O:32])[CH:39]=3)=[CH:7][CH:6]=2)[N:9]=[C:10]([C:20]([OH:29])([C:21]([F:22])([F:24])[F:23])[C:25]([F:26])([F:27])[F:28])[CH:11]=1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 27735423-(Methylsulfonyl)phenylboronic acidHCID 59631937HCID 59631937, compound

Product 1

HCID 59632552HCID 59632552, compoundYield 82%

Conditions

Temperature
80 °C

Procedure

A mixture of 2-[1-(4-bromophenyl)-5-(2-chlorophenyl)-1H-pyrazol-3-yl]-1,1,1,3,3,3-hexafluoro-propan-2-ol (100 mg, 020 mmol), 3-methanesulfonyl-phenylboronic acid (48 mg, 0.24 mmol), K2CO3 (83 mg, 0.60 mmol), Cl2Pd(dppf).DCM (16 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 3 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 50:50) to give the title compound (94 mg, 82%) as a white solid. 1H-NMR (DCM-d2): δ 8.12 (m, 1H), 7.92 (m, 1H), 7.87 (m, 1H), 7.67 (m, 1H), 7.61 (d, 2H), 7.33-7.47 (m, 6H), 6.74 (s, 1H), 5.25 (s, 1H), 3.07 (s, 3H); MS(ES): 575 [M+H]+.

Workup

  1. customDCM (16 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 50:50)

Sources & evidence

ORD record
ord-5e2e4aa6514a4d3589c74bb2928894b3
Source dataset
uspto-grants-2014_04
Patent number
US08703805B2

Reaction notes

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