4-Methoxybenzylamine → N-(4-methoxybenzyl)-5-bromo-3-(1-(2,3-dichlorophenyl)-1H-imidazol-2-yl)pyridin-2-amine

HRID 1518513Notes

Reaction equation

HRID 1518513 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH2:10])=[CH:5][CH:4]=1.[Br:11][C:12]1[CH:13]=[C:14]([C:19]2[N:20]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[C:25]=3[Cl:31])[CH:21]=[CH:22][N:23]=2)[C:15](Cl)=[N:16][CH:17]=1>O1CCOCC1.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH:10][C:15]2[C:14]([C:19]3[N:20]([C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[C:25]=4[Cl:31])[CH:21]=[CH:22][N:23]=3)=[CH:13][C:12]([Br:11])=[CH:17][N:16]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 754524-MethoxybenzylamineHCID 581798675-bromo-2-chloro-3-(1-(2,3-dichlorophenyl)-1H-imidazol-2-yl)pyridine

Product 1

HCID 58180101N-(4-methoxybenzyl)-5-bromo-3-(1-(2,3-dichlorophenyl)-1H-imidazol-2-yl)pyridin-2-amine

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of excess (4-methoxyphenyl)methanamine (0.2 mL) in dioxane (2 mL)was added 5-bromo-2-chloro-3-(1-(2,3-dichlorophenyl)-1H-imidazol-2-yl)pyridine (0.089 g, 0.222 mmol). The mixture was heated at 100° C. for 16 hours in a sealed reaction vessel. The mixture was then cooled, diluted with ethyl acetate, washed with saturated aqueous sodium bicarbonate, and the combined organics dried over sodium sulfate. After filtration and concentration, the residue was purified by flash chromatography (20% hexanes/methylene chloride to 25% ethyl acetate/methylene chloride to provide 0.065 g of N-(4-methoxybenzyl)-5-bromo-3-(1-(2,3-dichlorophenyl)-1H-imidazol-2-yl)pyridin-2-amine [LC-MS m/e=505.0 (M+H)]. Using the same procedure, N-(4-methoxybenzyl)-5-bromo-3-(1-(2,3-difluorophenyl)-1H-imidazol-2-yl)pyridin-2-amine and N-(4-methoxybenzyl)-5-bromo-3-(1-(3-chloro-2-fluorophenyl)-1H-imidazol-2-yl)pyridin-2-amine can be produced from 5-bromo-2-chloro-3-(1-(2,3-difluorophenyl)-1H-imidazol-2-yl)pyridine and 5-bromo-2-chloro-3-(1-(3-chloro-2-fluorophenyl)-1H-imidazol-2-yl)pyridine, respectively

Workup

  1. temperatureThe mixture was then cooled
  2. washwashed with saturated aqueous sodium bicarbonate
  3. dry with materialthe combined organics dried over sodium sulfate
  4. filtrationAfter filtration and concentration
  5. customthe residue was purified by flash chromatography (20% hexanes/methylene chloride to 25% ethyl acetate/methylene chloride

Sources & evidence

ORD record
ord-dd8ca78734784b3198ac7b9e4a07b2f9
Source dataset
uspto-grants-2012_07
Patent number
US08232406B2

Reaction notes

Loading…