تفاعل #466459

معادلة التفاعل

9-(5,6,7,8-Tetrahydro-[1,8]naphthyridin-2-yl)-3-(trifluoromethanesulfonyloxy)-non-2-enoic acid tert-butyl ester

9-(5,6,7,8-Tetrahydro-[1,8]naphthyridin-2-yl)-3-(trifluoromethane-sulfonyloxy)-non-2-enoic acid tert-butyl ester

phenylboronic acid

potassium carbonate

sodium hydrogen carbonate

→

29-7a

3-Phenyl-9-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-non-2-enoic acid tert-butyl ester

المذيبات

toluene

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةto cool to ambient temperature
2. 2
   استخلاصextracted with ethyl acetate
3. 3
   غسيلThe organic layer was washed with saturated aqueous sodium chloride
4. 4
   تجفيفdried with anhydrous magnesium sulfate
5. 5
   ترشيحfiltered
6. 6
   تركيزconcentrated at reduced pressure
7. 7
   أخرىThe resulting oil was purified by flash column chromatography over silica gel with 4:1 ethyl acetate/hexanes

الإجراء التجريبي

To a stirred solution of 9-(5,6,7,8-Tetrahydro-[1,8]naphthyridin-2-yl)-3-(trifluoromethanesulfonyloxy)-non-2-enoic acid tert-butyl ester 29-6 (100 mg, 0.20 mmol) in toluene (2.5 mL) was added palladium(tetrakis)-triphenylphosphine (23 mg, 0.020 mmol), phenylboronic acid (50 mg, 0.41 mmol), and potassium carbonate (56 mg, 0.41 mmol). The resulting suspension was heated at 90-100° C. for 2 hours, and then was allowed to cool to ambient temperature. The reaction mixture was then poured into saturated aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried with anhydrous magnesium sulfate, filtered, and concentrated at reduced pressure. The resulting oil was purified by flash column chromatography over silica gel with 4:1 ethyl acetate/hexanes to give 29-7a as a colorless oil.

المصدر