Water → HCID 15457070, compound

HRID 992879Notes

Reaction equation

HRID 992879 reaction equation
[H-].[Na+].[CH2:3]([OH:6])[C:4]#[CH:5].[Cl:7][C:8]1[C:13]([CH2:14]Br)=[CH:12][C:11]([C:16]2[C:17](=[O:27])[N:18]([CH3:26])[C:19]([C:22]([F:25])([F:24])[F:23])=[CH:20][CH:21]=2)=[C:10]([F:28])[CH:9]=1.O>CN(C=O)C>[Cl:7][C:8]1[C:13]([CH2:14][O:6][CH2:3][C:4]#[CH:5])=[CH:12][C:11]([C:16]2[C:17](=[O:27])[N:18]([CH3:26])[C:19]([C:22]([F:25])([F:24])[F:23])=[CH:20][CH:21]=2)=[C:10]([F:28])[CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7859Propargyl alcoholHCID 24758Sodium hydrideHCID 15457065HCID 15457065, compound

Product 1

HCID 15457070HCID 15457070, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

0.04 g (1.10 mmol) of sodium hydride was suspended in 5 ml of DMF, and 0.06 g (1.10 mmol) of propargyl alcohol was dropwise added thereto at room temperature, followed by stirring for 30 minutes. Then, 0.40 g (1.00 mmol) of 3-(4-chloro-2-fluoro-5-bromomethylphenyl)-1-methyl-6-trifluoromethyl-2(1H)-pyridone was dissolved in 5 ml of DMF, and dropwise added thereto, followed by stirring for 2 hours. The reaction mixture was poured into water and extracted with ethyl ether. The extract was dried over magnesium sulfate. Then, the solvent was distilled off under reduced pressure. Then, the obtained residue was purified by silica gel column chromatography to obtain 0.34 g (yield: 91%) of the desired product. Melting point: 99-101° C.

Workup

  1. customat room temperature
  2. additiondropwise added
  3. stirringby stirring for 2 hours
  4. extractionextracted with ethyl ether
  5. dry with materialThe extract was dried over magnesium sulfate
  6. distillationThen, the solvent was distilled off under reduced pressure
  7. customThen, the obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-98da191ab0da446f809cbbcc5ecc1c06
Source dataset
uspto-grants-2002_10
Patent number
US06472348B1

Reaction notes

Loading…