Water → 1-[(2E)-3-(4-tert-butylphenyl)-3-(5-chloro-6-methoxypyridin-2-yl)prop-2-en-1-yl]-3-methylimidazolidin-2-one

HRID 70702Notes

Reaction equation

HRID 70702 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][NH:4][C:3]1=[O:7].C(=O)([O-])[O-].[K+].[K+].Br[CH2:15]/[CH:16]=[C:17](/[C:28]1[N:33]=[C:32]([O:34][CH3:35])[C:31]([Cl:36])=[CH:30][CH:29]=1)\[C:18]1[CH:23]=[CH:22][C:21]([C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:20][CH:19]=1.O>C(#N)C>[C:24]([C:21]1[CH:22]=[CH:23][C:18](/[C:17](/[C:28]2[CH:29]=[CH:30][C:31]([Cl:36])=[C:32]([O:34][CH3:35])[N:33]=2)=[CH:16]\[CH2:15][N:4]2[CH2:5][CH2:6][N:2]([CH3:1])[C:3]2=[O:7])=[CH:19][CH:20]=1)([CH3:27])([CH3:26])[CH3:25]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 5676001-Methylimidazolidin-2-oneHCID 584528146-[(1E)-3-Bromo-1-(4-tert-butylphenyl)prop-1-en-1-yl]-3-chloro-2-methoxypyridine

Product 1

HCID 674008461-[(2E)-3-(4-tert-butylphenyl)-3-(5-chloro-6-methoxypyridin-2-yl)prop-2-en-1-yl]-3-methylimidazolidin-2-oneYield 10.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-Methyl-2-imidazolidinone (80 mg) and potassium carbonate (135 mg) were added to a solution of 6-[(1E)-3-bromo-1-(4-tert-butylphenyl)prop-1-en-1-yl]-3-chloro-2-methoxypyridine (123 mg) in acetonitrile (2 mL), and the mixture was stirred at room temperature for 3.5 days. The reaction solution was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and filtered, after which the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1→0:10) to give 1-[(2E)-3-(4-tert-butylphenyl)-3-(5-chloro-6-methoxypyridin-2-yl)prop-2-en-1-yl]-3-methylimidazolidin-2-one as a yellow oil (13 mg, 10%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customafter which the solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1→0:10)

Sources & evidence

ORD record
ord-f4cff6f9ac5f45c89ec9b1b339f11f1c
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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