Potassium Carbonate → HCID 59631704, compound

HRID 2369036Notes

Reaction equation

HRID 2369036 reaction equation
Br[C:2]1[S:6][C:5]([C:7]2[N:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:18])[N:10]=[C:9]([C:19]([OH:28])([C:24]([F:27])([F:26])[F:25])[C:20]([F:23])([F:22])[F:21])[CH:8]=2)=[CH:4][CH:3]=1.[CH3:29][S:30]([C:33]1[CH:34]=[C:35](B(O)O)[CH:36]=[CH:37][CH:38]=1)(=[O:32])=[O:31].C([O-])([O-])=O.[K+].[K+]>>[Cl:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[N:11]1[C:7]([C:5]2[S:6][C:2]([C:37]3[CH:36]=[CH:35][CH:34]=[C:33]([S:30]([CH3:29])(=[O:32])=[O:31])[CH:38]=3)=[CH:3][CH:4]=2)=[CH:8][C:9]([C:19]([OH:28])([C:24]([F:27])([F:25])[F:26])[C:20]([F:21])([F:23])[F:22])=[N:10]1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 27735423-(Methylsulfonyl)phenylboronic acidHCID 59631635HCID 59631635, compound

Product 1

HCID 59631704HCID 59631704, compoundYield 34.4%

Conditions

Temperature
80 °C

Procedure

A mixture of 2-[5-(5-bromothiophen-2-yl)-1-(2-chlorophenyl)-1H-pyrazol-3-yl]-1,1,1,3,3,3-hexafluoro-propan-2-ol (84 mg, 0.17 mmol), 3-methanesulfonyl-phenylboronic acid (42 mg, 0.21 mmol), K2CO3 (70 mg, 0.51 mmol), Cl2Pd(dppf).DCM (21 mg, 15 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 (34 mg) as a white solid. 1H-NMR (DCM-d2): δ 8.03 (m, 1H), 7.83 (m, 1H), 7.76 (m, 1H), 7.55-7.62 (m, 4H), 7.49-7.54 (m, 1H), 7.29 (d, 1H), 6.91 (d, 1H), 6.86 (s, 1H), 5.10 (s, 1H), 3.05 (s, 3H); MS(ES): 581 [M+H]+.

Workup

  1. customDCM (21 mg, 15 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-569df983a6c441e08cc83fdea4ef10cc
Source dataset
uspto-grants-2014_04
Patent number
US08703805B2

Reaction notes

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