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Potassium Carbonate → 1-(3-fluoro-4-(morpholinomethyl)phenyl)-3,5-dimethylpyridin-2(1H)-one

HRID 56074
Notes
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Reaction equation

HRID 56074 reaction equation
[CH3:1][C:2]1[C:3](=[O:9])[NH:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.[F:10][C:11]1[CH:23]=[C:22](I)[CH:21]=[CH:20][C:12]=1[CH2:13][N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.C([O-])([O-])=O.[K+].[K+]>[Cu]I.CN(C=O)C>[F:10][C:11]1[CH:23]=[C:22]([N:4]2[CH:5]=[C:6]([CH3:8])[CH:7]=[C:2]([CH3:1])[C:3]2=[O:9])[CH:21]=[CH:20][C:12]=1[CH2:13][N:14]1[CH2:15][CH2:16][O:17][CH2:18][CH2:19]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 123485383,5-Dimethyl-1,2-dihydropyridin-2-oneHCID 900233414-(2-Fluoro-4-iodobenzyl)morpholine

Product 1

HCID 729506741-(3-fluoro-4-(morpholinomethyl)phenyl)-3,5-dimethylpyridin-2(1H)-oneYield 50%

Reagents, catalysts & solvents 2

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Catalyst
HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3,5-dimethylpyridin-2(1H)-one (0.22 g, 1.80 mmol), 4-(2-fluoro-4-iodobenzyl)morpholine (0.58 g, 1.80 mmol), K2CO3 (2.48 g, 18 mmol), CuI (0.02 g, 0.1 mmol) and DMF (3 mL) was refluxed under N2. The reaction process was monitored by TLC. The reaction mixture was cooled to rt and filtered. To the filtrate was added H2O (10 mL) and CH2Cl2 (20 mL). The CH2Cl2 layer was separated, and the aqueous layer was extracted with CH2Cl2 (20 mL×2). The combined organic phases were dried over Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1) to give the title compound as a white solid (0.28 g, 50%). The compound was characterized by the following spectroscopic data:

Workup

  1. temperaturewas refluxed under N2
  2. filtrationfiltered
  3. additionTo the filtrate was added H2O (10 mL) and CH2Cl2 (20 mL)
  4. customThe CH2Cl2 layer was separated
  5. extractionthe aqueous layer was extracted with CH2Cl2 (20 mL×2)
  6. dry with materialThe combined organic phases were dried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1)

Sources & evidence

ORD record
ord-148628301ca345b98164581c419f0219
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09434695B2

Reaction notes

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