Potassium Carbonate → 1-(3-Chloro-5-iodo-benzyl)-2-(4-fluoro-phenoxymethyl)-1H-imidazole

HRID 2101517Notes

Reaction equation

HRID 2101517 reaction equation
[F:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][CH2:7][C:8]2[NH:9][CH:10]=[CH:11][N:12]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:22][C:23]1[CH:28]=[C:27]([I:29])[CH:26]=[C:25]([Cl:30])[CH:24]=1>CN(C=O)C>[Cl:30][C:25]1[CH:24]=[C:23]([CH:28]=[C:27]([I:29])[CH:26]=1)[CH2:22][N:12]1[CH:11]=[CH:10][N:9]=[C:8]1[CH2:7][O:6][C:5]1[CH:13]=[CH:14][C:2]([F:1])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 578015153-Chloro-5-iodobenzyl bromideHCID 578015272-(4-Fluoro-phenoxymethyl)-1H-imidazole

Product 1

HCID 119553431-(3-Chloro-5-iodo-benzyl)-2-(4-fluoro-phenoxymethyl)-1H-imidazoleYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(4-fluoro-phenoxymethyl)-1H-imidazole in DMF was added freshly ground K2CO3 followed by bromomethyl-3-chloro-5-iodo-benzene. The reaction mixture was stirred at room temperature until most of starting material was consumed. The reaction mixture was then diluted with ethyl acetate and washed with water. The organic phase was dried over MgSO4 and concentrated. The resulting residue was purified by silica gel preparative TLC using CH2Cl2:MeOH 95:5 as an eluent to afford the title compound (275 mg, 60%); MS m/z 442 [C17H13ClFIN2O+H]+.

Workup

  1. customwas consumed
  2. additionThe reaction mixture was then diluted with ethyl acetate
  3. washwashed with water
  4. dry with materialThe organic phase was dried over MgSO4
  5. concentrationconcentrated
  6. customThe resulting residue was purified by silica gel preparative TLC

Sources & evidence

ORD record
ord-2534d9c34f4443e5a0c00945fdd09f12
Source dataset
uspto-grants-2009_08
Patent number
US07572921B2

Reaction notes

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