Potassium Carbonate → HCID 59251324, compound

HRID 1466430Notes

Reaction equation

HRID 1466430 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:11]([C:13]([CH3:17])([CH3:16])[CH2:14][OH:15])[N:10]=[C:9]2[C:18]2[C:23]([Cl:24])=[CH:22][CH:21]=[CH:20][C:19]=2[Cl:25])=[CH:4][CH:3]=1.[CH3:26][S:27]([C:30]1[CH:31]=[C:32](B(O)O)[CH:33]=[CH:34][CH:35]=1)(=[O:29])=[O:28].C(=O)([O-])[O-].[K+].[K+]>>[Cl:25][C:19]1[CH:20]=[CH:21][CH:22]=[C:23]([Cl:24])[C:18]=1[C:9]1[N:8]([C:5]2[CH:6]=[CH:7][C:2]([C:34]3[CH:33]=[CH:32][CH:31]=[C:30]([S:27]([CH3:26])(=[O:29])=[O:28])[CH:35]=3)=[CH:3][CH:4]=2)[CH:12]=[C:11]([C:13]([CH3:17])([CH3:16])[CH2:14][OH:15])[N:10]=1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 27735423-(Methylsulfonyl)phenylboronic acidHCID 59251353HCID 59251353, compound

Product 1

HCID 59251324HCID 59251324, compoundYield 14.8%

Conditions

Temperature
60 °C

Procedure

A stirred mixture of 2-[1-(4-bromophenyl)-2-(2,6-dichlorophenyl)-1H-imidazol-4-yl]-2-methyl-propan-1-ol (202 mg, 0.46 mmol), 3-methanesulfonyl-phenylboronic acid (92 mg, 0.46 mmol), potassium carbonate (0.19 g, 1.4 mmol), Cl2Pd(dppf).DCM (19 mg, 5 mol %) and H2O (0.25 mL) in DME (2.5 mL) was sparged with Argon for 5 min and then heated at 60° C. as a sealed flask. After 30 min the reaction mixture was concentrated under reduced pressure and purified by chromatography (silica, EtOAc/Hex, 40:60 to 75:25) to give the title compound (35 mg) as a white solid. 1H-NMR (DCM-d2): δ 8.10 (m, 1H), 7.91 (d, 1H), 7.85 (d, 1H), 7.66 (m, 1H), 7.60 (d, 2H), 7.29-7.37 (m, 5H), 7.10 (s, 1H), 3.79 (br s, 1H), 3.62 (s, 2H), 3.06 (s, 3H), 1.36 (s, 6H); MS (ES): 515, 517 [M+H]+.

Workup

  1. customDCM (19 mg, 5 mol %) and H2O (0.25 mL) in DME (2.5 mL) was sparged with Argon for 5 min
  2. concentrationAfter 30 min the reaction mixture was concentrated under reduced pressure
  3. custompurified by chromatography (silica, EtOAc/Hex, 40:60 to 75:25)

Sources & evidence

ORD record
ord-a7b0b96c3dab44028cc0a921f610f169
Source dataset
uspto-grants-2015_04
Patent number
US09000022B2

Reaction notes

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