تفاعل #1748320

معادلة التفاعل

dimethylformamide

tert-butyl 5-bromonicotinate

potassium carbonate

3,4-methylenedioxy-phenyl boronic acid

→

solid

المردود 88.1%

Tert-Butyl 5-(3,4-methylenedioxyphenyl)nicotinate

المردود 88.1%

المذيبات

water

ظروف التفاعل

المعالجة

1. 1
   أخرىIn a flask was placed
2. 2
   أخرىThe flask was purged with nitrogen
3. 3
   درجة الحرارةheated
4. 4
   درجة الحرارةto cool
5. 5
   workup.ADDITIONdiluted with water (350 mL)
6. 6
   استخلاصextracted with CH2Cl2 (4X)
7. 7
   غسيلThe combined extracts was washed with water
8. 8
   تجفيفdried (MgSO4)
9. 9
   تركيزconcentrated in vacuo
10. 10
    أخرىThe crude residue was purified by flash chromatography on silica (gradient, CH2Cl2 to 50% ether/CH2Cl2)

الإجراء التجريبي

In a flask was placed tert-butyl 5-bromonicotinate (1.00 g, 3.87 mmol), 10% w/w palladium on carbon (210 mg, ˜0.2 mmol Pd), potassium carbonate (1.10 g, 7.96 mmol), 3,4-methylenedioxy-phenyl boronic acid (0.96 g, 5.79 mmol), dimethylformamide (50 mL) and water (250 L). The flask was purged with nitrogen and then heated, with stirring, to 90° C. for 15 hr. The reaction mixture was allowed to cool, diluted with water (350 mL) and extracted with CH2Cl2 (4X). The combined extracts was washed with water, dried (MgSO4) and concentrated in vacuo. The crude residue was purified by flash chromatography on silica (gradient, CH2Cl2 to 50% ether/CH2Cl2) to provide an off-white solid (1.02 g, 88%).

المصدر