Potassium Carbonate → 1-((6-chloropyridin-3-yl)methyl)-5-(4-methoxyphenyl)pyridin-2(1H)-one

HRID 1948277Notes

Reaction equation

HRID 1948277 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.[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23]Cl)=[CH:19][N:18]=1.C([O-])([O-])=O.[K+].[K+]>C1COCC1>[Cl:16][C:17]1[N:18]=[CH:19][C:20]([CH2:23][N:13]2[CH:14]=[C:9]([C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[CH:10]=[CH:11][C:12]2=[O:15])=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1554792-Chloro-5-(chloromethyl)pyridineHCID 200814975-(4-Methoxyphenyl)pyridin-2(1H)-one

Product 1

HCID 862293191-((6-chloropyridin-3-yl)methyl)-5-(4-methoxyphenyl)pyridin-2(1H)-oneYield 75.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-(4-Methoxyphenyl)pyridine-2(1H)-one (4.20 mmol, 0.85 g), 2-chloro-5-(chloromethyl)pyridine (1.5 eq, 6.30 mmol, 1.02 g), K2CO3 (2 eq, 8.40 mmol, 1.17 g) in THF (10 mL) were heated at 70° C. for 2 hours. Then, the reaction was cooled to room temperature. The suspension was filtered off and the filtrate was evaporated under reduced pressure. The residue was puridied by short open column chromatography CH2Cl2/MeOH(NH3)sat. 1% yielding 1-((6-chloropyridin-3-yl)methyl)-5-(4-methoxyphenyl)pyridin-2(1H)-one as white solid (1.04 g, 75%)

Workup

  1. filtrationThe suspension was filtered off
  2. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-eb465f2bb15e4014be2f692679023833
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Reaction notes

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