1,10-Phenanthroline → 4-(2-Dimethylaminomethyl-imidazol-1-yl)-benzoic acid methyl ester

HRID 1242047Notes

Reaction equation

HRID 1242047 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7](I)=[CH:6][CH:5]=1.[NH:12]1[CH:16]=[CH:15][N:14]=[C:13]1[CH2:17][N:18]([CH3:20])[CH3:19].C([O-])([O-])=O.[K+].[K+].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1>CS(C)=O.[Cu]I.CO.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([N:12]2[CH:16]=[CH:15][N:14]=[C:13]2[CH2:17][N:18]([CH3:20])[CH3:19])=[CH:6][CH:5]=1

Participants

9

Reactant 4

HCID 13181,10-PhenanthrolineHCID 11430Potassium CarbonateHCID 69273Methyl 4-iodobenzoateHCID 11457689((1H-imidazol-2-yl)methyl)dimethylamine

Product 1

HCID 694915164-(2-Dimethylaminomethyl-imidazol-1-yl)-benzoic acid methyl esterYield 40%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

Part G. 4-Iodo-benzoic acid methyl ester (1.42 g, mmol) and (1H-imidazol-2-ylmethyl)-dimethyl-amine (0.68 g, mmol) were stirred in DMSO (3.5 mL) under N2. K2CO3 (1.52 g, mmol) was added followed by the addition of CuI (0.52 g, mmol) and 1,10-phenanthroline (0.46 g, mmol). The reaction mixture was heated at 120–125° C. for 2 h. After cooling, EtOAc was added. It was washed with dil. NH3H2O, H2O, brine, dried over MgSO4, filtered, and concentrated to dryness. The residue was purified by FCC (silica gel, CH2Cl2:EtOAc=1:0 to 0:1, then 10% MeOH) to give pure 4-(2-dimethylaminomethyl-imidazol-1-yl)-benzoic acid methyl ester (0.56 g, yield 40%). 1H NMR (CDCl3) δ 7.84 (d, J=8.4 Hz, 2H), 7.40 (d, J=8.4 Hz, 2H), 6.87 (d, J=0.9 Hz, 1H), 6.80 (d, J=0.9 Hz, 1H), 3.65 (s, 3H), 3.10 (s, 2H), 1.96 (s, 6H) ppm.

Workup

  1. temperatureThe reaction mixture was heated at 120–125° C. for 2 h
  2. temperatureAfter cooling
  3. washIt was washed with dil. NH3H2O, H2O, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe residue was purified by FCC (silica gel, CH2Cl2

Sources & evidence

ORD record
ord-0a30768387e34a2d87812c38ad90e545
Source dataset
uspto-grants-2006_10
Patent number
US07115646B2

Reaction notes

Loading…