Propargyl bromide → HCID 19082073, compound

HRID 963296Notes

Reaction equation

HRID 963296 reaction equation
[Cl:1][C:2]1[C:3]([CH2:29][CH3:30])=[N:4][CH:5]=[CH:6][C:7]=1[NH:8][C:9](=[O:28])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][N:19]=2)=[CH:13][CH:12]=1.[H-].[Na+].[CH2:33](Br)[C:34]#[CH:35]>CN(C)C(=O)C>[Cl:1][C:2]1[C:3]([CH2:29][CH3:30])=[N:4][CH:5]=[CH:6][C:7]=1[N:8]([CH2:35][C:34]#[CH:33])[C:9](=[O:28])[CH2:10][C:11]1[CH:12]=[CH:13][C:14]([O:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:25])([F:26])[F:27])=[CH:20][N:19]=2)=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 7842Propargyl bromide2×HCID 24758Sodium hydrideHCID 19082084HCID 19082084, compound

Product 1

HCID 19082073HCID 19082073, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

1.0 g (2.3 mmol) of N-(3-chloro-2-ethylpyridin-4-yl)-4-[(5-trifluoromethylpyridin-2-yl)oxy]phenylacetamide was dissolved in 5 ml of N,N-dimethylacetamide, and the solution was stirred at room temperature. Then, 0.067 g (2.8 mmol) of sodium hydride was gradually added thereto, and the mixture was further stirred for one hour at room temperature. Then, 10.3 (2.5 mmol) of propargyl bromide was added thereto, and the mixture was stirred for one hour at room temperature. Then, 0.3 g (2.5 mmol) of propargyl bromide was further added thereto, and the mixture was stirred for one hour at a temperature of from 50° to 60° C. Then, the reaction solution was poured into ice water and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous magnesium sulfate. Then, ethyl acetate was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate) and then purified by high performance liquid chromatography to obtain 0.5 g of the desired product as a brown viscous substance (refractive index nD20 =1.35619).

Workup

  1. stirringthe mixture was further stirred for one hour at room temperature
  2. stirringthe mixture was stirred for one hour at room temperature
  3. stirringthe mixture was stirred for one hour at a temperature of from 50° to 60° C
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThen, ethyl acetate was distilled off under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate)
  9. custompurified by high performance liquid chromatography

Sources & evidence

ORD record
ord-2fec9fbf160e45bfac354dcdd886741f
Source dataset
uspto-grants-1998_06
Patent number
US05763463

Reaction notes

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