تفاعل #70419

معادلة التفاعل

3-chloro-6-(4-methanesulfonylphenoxymethyl)pyridazine

tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylate

cesium carbonate

water

→

title compound

المردود 14.0%

tert-Butyl 4-[6-(4-methanesulfonylphenoxymethyl)-pyridazin-3-yl]-3,6-dihydro-2H-pyridine-1-carboxylate

المردود 14.0%

المذيبات

N,N-dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةto cool to room temperature
2. 2
   استخلاصextracted with ethyl acetate
3. 3
   غسيلThe organic layer was washed with brine
4. 4
   تجفيفdried over anhydrous sodium sulfate
5. 5
   تركيزconcentrated under reduced pressure
6. 6
   أخرىThe residue was purified by silica gel column chromatography (chloroform/ethyl acetate=10/1 and hexane/ethyl acetate=1/2)

الإجراء التجريبي

To a solution of 3-chloro-6-(4-methanesulfonylphenoxymethyl)pyridazine (79 mg, 0.26 mmol) and tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylate (82 mg, 0.26 mmol) in dry N,N-dimethylformamide (3 mL) was added tetrakis(triphenylphosphine)palladium (9.0 mg, 7.9 μmol) and cesium carbonate (129 mg, 0.397 mmol). The mixture was stirred at 80° C. for 2 hours, allowed to cool to room temperature, poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/ethyl acetate=10/1 and hexane/ethyl acetate=1/2) to give the title compound as a white crystal (16 mg, yield 14%).

المصدر