Reaction #1563892

Reaction equation

Compound 25

2-amino-N-(2-methoxyphenyl)-6-(4-nitrophenylthi-o)benzamide

potassium carbonate

diisopropyl(bromomethyl)phosphonate

→

solid

Yield 41.0%

diisopropyl(((2-((2-methoxyphenyl)carbamoyl)-3-((4-nitro-phenyl)thio)phenyl)amino)methyl)phosphonate

Yield 41.0%

Solvents

MeCN

Conditions

Workup

1. 1
   Concentrationthe reaction mixture was concentrated under reduced pressure
2. 2
   workup.ADDITIONThe crude residue was diluted by ethyl acetate (50 mL)
3. 3
   Washwashed with water (2×10 mL)
4. 4
   DryingThen it was dried over anhydrous Na2SO4
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated under reduced pressure
7. 7
   OtherThe residue was purified by silica gel column chromatography (1:4 v/v ethyl acetate/petroleum ether)

Procedure

Compound 25 (1.0 equiv.) was dissolved in MeCN (40 mL) and treated with anhydrous potassium carbonate (2.0 equiv.) at room temperature. To this mixture diisopropyl(bromomethyl)phosphonate (1.2 equiv.) was added via a micro syringe. After being stirred for 4 Hours at 60° C., the reaction mixture was concentrated under reduced pressure. The crude residue was diluted by ethyl acetate (50 mL), and washed with water (2×10 mL). Then it was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (1:4 v/v ethyl acetate/petroleum ether) to provide a yellow solid (235.2 mg, 41% yield).

Source