Potassium Carbonate → HCID 59599698, compound

HRID 2266779Notes

Reaction equation

HRID 2266779 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:9].Cl[CH2:11][C:12]1[N:13]([C:17]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:14]=[CH:15][N:16]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.CN(C=O)C.CCOC(C)=O>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[O:9][CH2:11][C:12]1[N:13]([C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:14]=[CH:15][N:16]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 808792,3-DifluorophenolHCID 54394968HCID 54394968, compound

Product 1

HCID 59599698HCID 59599698, compoundYield 95.2%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 17824068DMF dimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 2,3-difluorophenol (109 mg) at room temperature in dimethylformamide DMF (5 ml) under an argon atmosphere were added 2-chloromethyl-1-trityl-1H-imidazole (200 mg) and potassium carbonate (193 mg). The mixture was heated to 80° C. and stirring was continued overnight. The brown suspension was cooled to room temperature, diluted with EtOAc and washed with 1 N NaOH. The aqueous phase was back extracted with EtOAc. The combined organics were washed with H2O and brine, dried over MgSO4, filtered and concentrated. The crude product was purified by column chromatography (silica gel; gradient:cyclohexane→cyclohexane/EtOAc 55:45) to give 2-(2,3-difluoro-phenoxymethyl)-1-trityl-1H-imidazole (240 mg) as a light yellow gum. MS (ISP): 453.0 ([M+H]+)

Workup

  1. temperatureThe brown suspension was cooled to room temperature
  2. washwashed with 1 N NaOH
  3. extractionThe aqueous phase was back extracted with EtOAc
  4. washThe combined organics were washed with H2O and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by column chromatography (silica gel; gradient:cyclohexane→cyclohexane/EtOAc 55:45)

Sources & evidence

ORD record
ord-4dad1007718b40e4b227fea4544ebfc4
Source dataset
uspto-grants-2010_12
Patent number
US07858653B2

Reaction notes

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