تفاعل #43605

معادلة التفاعل

(5-({[4-(Methyloxy)phenyl]methyl}oxy)-4-{[(trifluoromethyl)sulfonyl]oxy}-2-pyridinyl)methyl acetate

triethylamine

trimethylsilyl acetylene

→

desired compound

المردود 96.0%

{5-({[4-(Methyloxy)phenyl]methyl}oxy)-4-[(trimethylsilyl)ethynyl]-2-pyridinyl}methyl Acetate

المردود 96.0%

المذيبات

acetonitrile

ظروف التفاعل

المعالجة

1. 1
   أخرىThe mixture was then degassed several times
2. 2
   درجة الحرارةto cool
3. 3
   ترشيحfiltered
4. 4
   تركيزThe filtrate was concentrated in vacuo
5. 5
   أخرىthe residue partitioned between ethyl acetate and water
6. 6
   أخرىThe organic layer was dried
7. 7
   أخرىthen evaporated to dryness

الإجراء التجريبي

(5-({[4-(Methyloxy)phenyl]methyl}oxy)-4-{[(trifluoromethyl)sulfonyl]oxy}-2-pyridinyl)methyl acetate (10 g, 23 mmol) (for a synthesis see WO2004058144, Example 60(d)) was dissolved in acetonitrile (400 ml) and triethylamine (65 ml) and treated with trimethylsilyl acetylene (10 ml, 69 mmol). The mixture was then degassed several times and put under an atmosphere of argon. Copper(I) iodide (0.44 g, 2,3 mmol) and bis(triphenylphosphine)palladium(II) chloride (0.645 g, 0.9 mmol) was added and the mixture heated at 45° C. for 18 h. The mixture was allowed to cool and filtered. The filtrate was concentrated in vacuo and the residue partitioned between ethyl acetate and water. The organic layer was dried then evaporated to dryness. Chromatography on silica gel eluting with 40-60 petrol and ethyl acetate gradient provided the desired compound (8.45 g, 96%).

المصدر