تفاعل #304392

معادلة التفاعل

5-ethoxymethoxy-benzofuran boronic acid

5-Ethoxymethoxy-benzofuran-2-boronic acid

(6-bromo-2-nitro-pyridin-3-yl)-methyl-carbamic acid tert-butyl ester

(6-Bromo-2-nitro-pyridin-3-yl)-methyl-carbamic acid tert-butyl ester

Et3N

→

title compound 8

المردود 84.3%

[6-(5-Ethoxymethoxy-benzofuran-2-yl)-2-nitro-pyridin-3-yl]-methyl-carbamic acid tert-butyl ester

المردود 84.3%

المذيبات

ethanol

ظروف التفاعل

المعالجة

1. 1
   أخرىVolatiles were removed under reduced pressure
2. 2
   workup.ADDITIONThe residue was diluted with water (15 mL)
3. 3
   استخلاصthe mixture was extracted with ethyl acetate (3×50 mL)
4. 4
   غسيلThe combined organic extracts were washed with water, brine
5. 5
   تجفيفdried over Na2SO4
6. 6
   تركيزconcentrated under reduced pressure
7. 7
   أخرىThe crude product was purified by flash column chromatography
8. 8
   أخرىEvaporation of solvent

الإجراء التجريبي

To a degassed solution of 5-ethoxymethoxy-benzofuran boronic acid (4) (140 mg, 0.593 mmol) in ethanol (10 mL), (6-bromo-2-nitro-pyridin-3-yl)-methyl-carbamic acid tert-butyl ester (7) (151 mg, 0.455 mmol), Pd(PPh3)2Cl2 (42 mg, 0.059 mmol) and Et3N (127 μL, 0.909 mmol) were added. The reaction mixture was stirred at 100° C. for 30 minutes in a microwave reactor. Volatiles were removed under reduced pressure. The residue was diluted with water (15 mL) and the mixture was extracted with ethyl acetate (3×50 mL). The combined organic extracts were washed with water, brine, dried over Na2SO4, and concentrated under reduced pressure. The crude product was purified by flash column chromatography using 20% ethyl acetate in hexane. Evaporation of solvent gave title compound 8 (170 mg) as a pale yellow solid.

المصدر