Potassium Carbonate → HCID 68668369, compound

HRID 216366Notes

Reaction equation

HRID 216366 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:43])([CH2:13][C:14]2[N:15]([C:24]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:16]=[C:17]([CH2:19][C:20]([CH3:23])([CH3:22])[CH3:21])[N:18]=2)[C:9]([F:12])([F:11])[F:10])=[CH:4][CH:3]=1.[NH:44]1[CH:48]=[CH:47][N:46]=[N:45]1.C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1=O.O.[Cu]I>[CH3:21][C:20]([CH3:23])([CH3:22])[CH2:19][C:17]1[N:18]=[C:14]([CH2:13][C:8]([C:5]2[CH:6]=[CH:7][C:2]([N:45]3[N:46]=[CH:47][CH:48]=[N:44]3)=[CH:3][CH:4]=2)([OH:43])[C:9]([F:12])([F:11])[F:10])[N:15]([C:24]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:16]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 68668430HCID 68668430, compoundHCID 178418936HCID 178418936, compound

Product 1

HCID 68668369HCID 68668369, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of copper (I) iodide (1 mg, 0.01 mmol), 2-(4-bromophenyl)-3-[4-(2,2-dimethylpropyl)-1-trityl-1H-imidazol-2-yl]-1,1,1-trifluoropropan-2-ol (50 mg, 0.08 mmol), 1,2,3-triazole (11 mg, 0.15 mmol) and potassium carbonate (21 mg, 0.15 mmol) in N-methylpyrrolidinone (1 mL) were irradiated in a microwave reactor at 195° C. for 1 h. The reaction mixture was diluted with water and extracted with ethyl acetate. The combined organic phases were dried (magnesium sulfate), filtered and concentrated in vacuo. High pressure liquid chromatography (KR100-5C18 100×21.2 mm column) eluting with 10-100% acetonitrile/water containing 0.1% trifluoroacetic acid afforded 3-[4-(2,2-dimethylpropyl)-1-trityl-1H-imidazol-2-yl]-1,1,1-trifluoro-2-[4-(2H-1,2,3-triazol-2-yl)phenyl]propan-2-ol.

Workup

  1. customwere irradiated in a microwave reactor at 195° C. for 1 h
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic phases were dried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. washHigh pressure liquid chromatography (KR100-5C18 100×21.2 mm column) eluting with 10-100% acetonitrile/water containing 0.1% trifluoroacetic acid

Sources & evidence

ORD record
ord-d1438e3082ec4f2eaf11346ddd7e2dab
Source dataset
uspto-grants-2012_06
Patent number
US08193228B2

Reaction notes

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