Potassium Carbonate → 1-[4-(2,2-dimethylpropyl)-1-trityl-1H-imidazol-2-yl]-2-[4-(1-methyl-1H-pyrazol-4-yl)phenyl]propan-2-ol

HRID 216361Notes

Reaction equation

HRID 216361 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:40])([CH3:39])[CH2:9][C:10]2[N:11]([C:20]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:12]=[C:13]([CH2:15][C:16]([CH3:19])([CH3:18])[CH3:17])[N:14]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:47][N:48]1[CH:52]=[C:51](B2OC(C)(C)C(C)(C)O2)[CH:50]=[N:49]1>C1(C)C=CC=CC=1.CO.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[CH3:17][C:16]([CH3:19])([CH3:18])[CH2:15][C:13]1[N:14]=[C:10]([CH2:9][C:8]([C:5]2[CH:6]=[CH:7][C:2]([C:51]3[CH:50]=[N:49][N:48]([CH3:47])[CH:52]=3)=[CH:3][CH:4]=2)([OH:40])[CH3:39])[N:11]([C:20]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:12]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 591619942-(4-bromophenyl)-1-[4-(2,2-dimethylpropyl)-1-trityl-1H-imidazol-2-yl]propan-2-ol

Product 1

HCID 686676631-[4-(2,2-dimethylpropyl)-1-trityl-1H-imidazol-2-yl]-2-[4-(1-methyl-1H-pyrazol-4-yl)phenyl]propan-2-ol

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 21867641Toluene methanolSolvent

Conditions

Temperature
90 °C

Procedure

Palladium tetrakis(triphenylphosphine) (50 mg, 0.04 mmol) was added to a degassed, ambient temperature solution of 2-(4-bromophenyl)-1-[4-(2,2-dimethylpropyl)-1-trityl-1H-imidazol-2-yl]propan-2-ol (500 mg, 0.84 mmol), potassium carbonate (151 mg, 1.1 mmol) and 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (193 mg, 0.9 mmol) in toluene/methanol (10:1) (4.4 mL). After stirring at 90° C. for 2 hr, the reaction mixture was washed with water and brine, dried (sodium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 20-100% ethyl acetate/hexane afforded 1-[4-(2,2-dimethylpropyl)-1-trityl-1H-imidazol-2-yl]-2-[4-(1-methyl-1H-pyrazol-4-yl)phenyl]propan-2-ol.

Workup

  1. washthe reaction mixture was washed with water and brine
  2. dry with materialdried (sodium sulfate)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-480df72e01044cbfa634aabc5e7f7dc2
Source dataset
uspto-grants-2012_06
Patent number
US08193228B2

Reaction notes

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