تفاعل #304398

معادلة التفاعل

5-ethoxymethoxy-benzofuran boronic acid

5-Ethoxymethoxy-benzofuran-2-boronic acid

(5-bromo-6-nitro-pyridin-2-yl)-methyl-carbamic acid tert-butyl ester

(5-Bromo-6-nitro-pyridin-2-yl)-methyl-carbamic acid tert-butyl ester

Et3N

→

title compound 13

المردود 58.0%

[5-(5-Ethoxymethoxy-benzofuran-2-yl)-6-nitro-pyridin-2-yl]-methyl-carbamic acid tert-butyl ester

المردود 58.0%

المذيبات

ethanol

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe reaction mixture was cooled to 0° C.
2. 2
   أخرىVolatiles were removed under reduced pressure
3. 3
   workup.ADDITIONThe residue was diluted with water
4. 4
   استخلاصthe mixture was extracted with ethyl acetate
5. 5
   استخلاصThe organic extract
6. 6
   غسيلwas washed with brine
7. 7
   تركيزconcentrated under reduced pressure
8. 8
   أخرىThe crude product was purified by flash column chromatography
9. 9
   أخرىEvaporation of solvent

الإجراء التجريبي

To a degassed solution of 5-ethoxymethoxy-benzofuran boronic acid (4) (0.69 g, 2.63 mmol) in ethanol (17.5 mL), (5-bromo-6-nitro-pyridin-2-yl)-methyl-carbamic acid tert-butyl ester 12 (0.50 g, 1.51 mmol), Pd(PPh3)2Cl2 (0.14 g, 0.20 mmol) and Et3N (0.48 mL, 3.46 mmol) were added. The reaction mixture was stirred at 90° C. for 30 minutes. The reaction mixture was cooled to 0° C. and clear filtered. Volatiles were removed under reduced pressure. The residue was diluted with water and the mixture was extracted with ethyl acetate. The organic extract was washed with brine and concentrated under reduced pressure. The crude product was purified by flash column chromatography. Evaporation of solvent gave title compound 13 (58% yield).

المصدر