Potassium Carbonate → HCID 19430487, compound

HRID 1078035Notes

Reaction equation

HRID 1078035 reaction equation
[CH2:1]([C:3]1[N:4]=[C:5]([CH2:10][CH2:11][CH3:12])[NH:6][C:7]=1[CH:8]=[O:9])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[F:19][C:20]1[CH:27]=[C:26]([I:28])[CH:25]=[CH:24][C:21]=1[CH2:22]Br>CN(C=O)C>[F:19][C:20]1[CH:27]=[C:26]([I:28])[CH:25]=[CH:24][C:21]=1[CH2:22][N:6]1[C:7]([CH:8]=[O:9])=[C:3]([CH2:1][CH3:2])[N:4]=[C:5]1[CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 222404061-(Bromomethyl)-2-fluoro-4-iodobenzeneHCID 178440054HCID 178440054, compound

Product 1

HCID 19430487HCID 19430487, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Ethyl-2-propyl-1H-imidazole-5-carboxaldehyde (6.32 g, 38.0 mmol), potassium carbonate (10.57 g, 76.5 mmol), and 2-fluoro-4-iodobenzyl bromide (13.90 g of 86%, 38.0 mmol) were added together with 50 mL of DMF. The reaction mixture was stirred at room temperature overnight under N2. The solvent was removed in vacuo and the residue was partitioned between EtOAc and H2O. The two layers were separated. The aqueous layer was extracted with EtOAc. The combined organic mixture was washed with H2O and brine, dried over MgSO4 and concentrated. The crude product mixture was purified by flash chromatography (silica gel, 30-50% EtOAc/hexane) to yield 10.63 g orange oil (70%). MS m/e 401.0, [M+H]+ ; 1H NMR (300 MHz, CDCl3): δ 0.95 (t, 3H, CH3), 1.32 (t, 3H, CH3), 1.70 (m, 2H, CH2), 2.60 (m, 2H, CH2), 2.82 (q, 2H, CH2), 5.52 (s, 2H, CH2Ar), 6.42 (t, 1H, ArH), 7.38 (d, 1H, ArH), 7.42 (d, 1H, ArH), 9.73 (s, 1H, CHO). ##STR62##

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between EtOAc and H2O
  3. customThe two layers were separated
  4. extractionThe aqueous layer was extracted with EtOAc
  5. washThe combined organic mixture was washed with H2O and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe crude product mixture was purified by flash chromatography (silica gel, 30-50% EtOAc/hexane)

Sources & evidence

ORD record
ord-100ee97cedb0492589a3b1e13452dc64
Source dataset
uspto-grants-1996_08
Patent number
US05545651

Reaction notes

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