Dimethylformamide → HCID 15457052, compound

HRID 1385927Notes

Reaction equation

HRID 1385927 reaction equation
CN(C=O)C.[Cl:6][C:7]1[C:12]([OH:13])=[CH:11][C:10]([C:14]2[C:15](=[O:26])[N:16]([CH3:25])[C:17]([C:21]([F:24])([F:23])[F:22])=[C:18]([CH3:20])[CH:19]=2)=[C:9]([F:27])[CH:8]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:34](Br)[C:35]#[CH:36]>O>[Cl:6][C:7]1[C:12]([O:13][CH2:36][C:35]#[CH:34])=[CH:11][C:10]([C:14]2[C:15](=[O:26])[N:16]([CH3:25])[C:17]([C:21]([F:22])([F:23])[F:24])=[C:18]([CH3:20])[CH:19]=2)=[C:9]([F:27])[CH:8]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 15457051HCID 15457051, compound

Product 1

HCID 15457052HCID 15457052, compoundYield 53.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To 10 ml of DMF, 0.20 g (0.6 mmol) of 3-(4-chloro-2-fluoro-5-hydroxyphenyl)-1,5-dimethyl-6-trifluoromethyl-2(1H)-pyridone, 0.1 g (0.7 mmol) of potassium carbonate and 0.1 g (0.8 mmol) of propargyl bromide were added, followed by stirring at 60° C. for 2 hours. This reaction solution was poured into water and extracted with ethyl acetate. After washing with water, the organic layer was dried over anhydrous magnesium sulfate. Ethyl acetate was distilled off under reduced pressure, and then, the obtained residue was purified by silica gel column chromatography to obtain 0.12 g of the desired product (yield: 53%). Melting point: 107-108° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washAfter washing with water
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. distillationEthyl acetate was distilled off under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-818bc4ba9fe04ff08db4920e6c8e09d1
Source dataset
uspto-grants-2001_07
Patent number
US06265349B1

Reaction notes

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