تفاعل #1053262

معادلة التفاعل

product

1-((4S,5S)-2,2-Dimethyl-4-phenyl-[1,3]dioxan-5-yl)-3-(4-iodo-phenyl)-urea

pyridine-3-boronic acid

sodium carbonate

→

title compound

المردود 45.1%

1-((4S,5S)-2,2-Dimethyl-4-phenyl-[1,3]dioxan-5-yl)-3-(4-pyridin-3-yl-phenyl)-urea

المردود 45.1%

المذيبات

ethylene glycol dimethyl ether

dichloromethane

ethanol

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added
2. 2
   درجة الحرارةcooled to room temperature
3. 3
   غسيلwashed with water
4. 4
   تجفيفThe organic layers were dried over magnesium sulfate
5. 5
   ترشيحfiltered
6. 6
   تركيزconcentrated in vacuo
7. 7
   أخرىThe product was purified by chromatography (hexanes/ethyl acetate)

الإجراء التجريبي

To a stirred solution of 10 mg (0.0088 mmol) of tetrakis(triphenylphosphine)palladium(0) in ethylene glycol dimethyl ether (2.0 mL) was added 100 mg (0.22 mmol) of the product from Example 7. After stirring for 15 min, 27 mg (0.22 mmol) of pyridine-3-boronic acid dissolved in ethanol (0.20 mL) was added followed by 0.22 mL (0.44 mmol) of a 2 M sodium carbonate aqueous solution. The reaction mixture was heated to 80° C. for 12 h and then cooled to room temperature. The mixture was taken up in 10 mL of dichloromethane and washed with water. The organic layers were dried over magnesium sulfate, filtered and concentrated in vacuo. The product was purified by chromatography (hexanes/ethyl acetate) to yield 40 mg (45%) of the title compound.

المصدر