Acetonitrile → 5-(4-methoxyphenyl)-1-(2-phenoxyethyl)pyridin-2(1H)-one

HRID 1948199

Reaction equation

HRID 1948199 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[CH:11][C:12](=[O:15])[NH:13][CH:14]=2)=[CH:5][CH:4]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:23][CH2:24][O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(#N)C>C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[CH:11][C:12](=[O:15])[N:13]([CH2:23][CH2:24][O:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:14]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium Carbonate2×HCID 68526Benzene, (2-bromoethoxy)-2×HCID 200814975-(4-Methoxyphenyl)pyridin-2(1H)-one

Product 1

HCID 589669325-(4-methoxyphenyl)-1-(2-phenoxyethyl)pyridin-2(1H)-oneYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

According to Scheme 5 Step 2: To a solution of 5-(4-methoxyphenyl)-(1H)-pyridin-2-one (1 eq, 0.30 mmol, 60 mg) in THF (3 mL) was added K2CO3 (10 eq, 3.00 mmol, 0.41 g). The reaction was stirred at room temperature for 30 minutes then 1-(2-bromoethoxy)benzene (3 eq, 0.90 mmol, 0.18 g) was added. The reaction was stirred at 60° C. for 12 hours. After concentration of the solvent, acetonitrile (3 mL) was added followed by K2CO3 (10 eq, 3.00 mmol, 0.41 g) and 1-(2-bromoethoxy)benzene (10 eq, 3.00 mmol, 0.60 g) then the reaction was microwaved for 5 minutes at 180° C. The reaction was filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography over silica gel (AIT Flashsmart prepacked column 10 g SiO2) using CH2Cl2/AcOEt (80/20) as the eluent to afford 5-(4-methoxyphenyl)-1-(2-phenoxyethyl)pyridin-2(1H)-one (0.13 mmol, 42 mg, 44%) as a yellow oil.

Workup

  1. stirringThe reaction was stirred at 60° C. for 12 hours
  2. customthe reaction was microwaved for 5 minutes at 180° C
  3. filtrationThe reaction was filtered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by flash chromatography over silica gel (AIT Flashsmart prepacked column 10 g SiO2)

Sources & evidence

ORD record
ord-2aa05178150b4cd185800356bf605313
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Linked notes

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