Potassium Carbonate → HCID 68699101, compound

HRID 2236907Notes

Reaction equation

HRID 2236907 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=1.Br[C:10]1[CH:14]=[CH:13][S:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.[OH-].[NH4+].[Cu]I>[CH3:8][C:6]1[CH:5]=[CH:4][N:3]([C:10]2[CH:14]=[CH:13][S:12][CH:11]=2)[C:2](=[O:1])[CH:7]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 133833-BromothiopheneHCID 178428601HCID 178428601, compound

Product 1

HCID 68699101HCID 68699101, compoundYield 29.5%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolventHCID 14923Ammonium HydroxideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 2-hydroxy-4-methylpyridine (1.5 g, 14 mmol), 3-bromothiophene (4.5 g, 28 mmol), copper (I) iodide (0.27 g, 1.4 mmol), and potassium carbonate (1.9 g, 14 mmol) in N,N-dimethylformamide (30 mL) is heated in a 150° C. oil bath for 6 hours. After cooling to room temperature, the reaction mixture is diluted with 20% aqueous ammonium hydroxide solution and extracted 3× with diethyl ether. The combined extracts were washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give a crude oil, which is purified by flash chromatography (ethyl acetate/hexanes) to give 4-methyl-1-(3-thienyl)pyridin-2(1H)-one (0.79 g, 29%).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted 3× with diethyl ether
  3. washThe combined extracts were washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give a crude oil, which
  7. customis purified by flash chromatography (ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-6f7c42e013814cf1ac06e0fed3858409
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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