反应详情

A 0.138 g (0.349 mM) portion of 6-amino-4-(3-bromoanilino)[1]benzothieno[3,2-b]pyridine-3-carbonitrile is dissolved in 2 mL of tetrahydrofuran and 2 mL of dimethylformamide at 0° C. To this is added 0.042 g (0.583 mM) of acrylic acid, 0.105 g (0.575 mM) of N,N-diisopropylethylamine and 0.106 g (0.554 mM) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride with stirring under nitrogen. The reaction mixture is stirred for 48 hours at room temperature, and the solvent is removed under reduced pressure. The residue is worked up with water (3 mL) and extracted with methylene chloride (10 mL), dried with sodium sulfate and evaporated. Purification of the product is carried out by silica get chromatography, eluting with 20:1 chloroform/methanol. Further purification is achieved by preparative thin layer chromatography, eluting with the same solvent system. Finally, the product is washed with ether to provide 0.068 g (43%) of N-[4-(3-bromoanilino)-3-cyano[1]benzothieno[3,2-b]pyridin-6-yl]acrylamide, m.p. 286–287° C.

1. customat 0° C
2. stirringThe reaction mixture is stirred for 48 hours at room temperature
3. customthe solvent is removed under reduced pressure
4. extractionextracted with methylene chloride (10 mL)
5. dry with materialdried with sodium sulfate
6. customevaporated
7. customPurification of the product
8. customget chromatography
9. washeluting with 20:1 chloroform/methanol
10. customFurther purification
11. washeluting with the same solvent system
12. washFinally, the product is washed with ether