Potassium Carbonate → HCID 15947692, compound

HRID 1466428Notes

Reaction equation

HRID 1466428 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:11]([C:13]([OH:19])([CH3:18])[C:14]([F:17])([F:16])[F:15])[N:10]=[C:9]2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26]([F:29])([F:28])[F:27])=[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+]>>[F:15][C:14]([F:17])([F:16])[C:13]([C:11]1[N:10]=[C:9]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26]([F:29])([F:28])[F:27])[N:8]([C:5]2[CH:6]=[CH:7][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:3][CH:4]=2)[CH:12]=1)([OH:19])[CH3:18]

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 27735423-(Methylsulfonyl)phenylboronic acidHCID 59251600HCID 59251600, compound

Product 1

HCID 15947692HCID 15947692, compoundYield 91%

Conditions

Temperature
80 °C

Procedure

A mixture of 2-[1-(4-bromophenyl)-2-(2-trifluoromethyl-phenyl)-1H-imidazol-4-yl]-1,1,1-trifluoro-propan-2-ol (0.11 g, 0.23 mmol), 3-methanesulfonyl-phenylboronic acid (54 mg, 0.27 mmol), K2CO3 (95 mg, 0.69 mmol), Cl2Pd(dppf).DCM (15 mg, 8 mol %) and H2O (0.25 mL) in DME (2.5 mL) was sparged with Argon for 5 min and then heated at 80° C. as a sealed flask. After 90 min 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, 35:65 to 80:20) to give the title compound (116 mg, 89%) as a white solid. 1H-NMR (DCM-d2): δ 8.09 (m, 1H), 7.91 (m, 1H), 7.84 (m, 1H), 7.78 (d, 1H), 7.66 (m, 1H), 7.59 (d, 2H), 7.49-7.57 (m, 2H), 7.33 (m, 2H), 7.25 (d, 2H), 4.40 (s, 1H), 3.06 (s, 3H), 1.75 (s, 3H); MS (ES): 555 [M+H]+.

Workup

  1. customDCM (15 mg, 8 mol %) and H2O (0.25 mL) in DME (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, 35:65 to 80:20)

Sources & evidence

ORD record
ord-de70962b9d664e82af8e13bbf5d4fcd9
Source dataset
uspto-grants-2015_04
Patent number
US09000022B2

Reaction notes

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