تفاعل #641949

معادلة التفاعل

5-bromonicotinic acid

tert-butyl 5-bromonicotinate

dimethylacetoamide

→

tert-butyl 5-cyanonicotinate

ظروف التفاعل

المعالجة

1. 1
   ترشيحThe reaction solution was filtered by sellite, which
2. 2
   غسيلwas then washed with ethyl acetate
3. 3
   غسيلthe filtrate was washed with saturated saline
4. 4
   تجفيفThe organic layer was dried over with anhydrous sodium sulfate
5. 5
   تركيزconcentrated
6. 6
   أخرىThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1)

الإجراء التجريبي

Instead of the starting material of Reference Example 56, that is, the compound S55, the 5-bromonicotinic acid was used for the similar procedure as in Reference Example 56. To the obtained tert-butyl 5-bromonicotinate (22.4 g), dimethylacetoamide (112 ml), tris(dibenzylideneacetone)dipalladium (1.59 g), zinc cyanide (6.1 g), diphenylphosphinoferrocene (1.92 g), and zinc powder (0.68 g) were added and the mixture was stirred under argon atmosphere at 120° C. for 1.5 hours. The reaction solution was filtered by sellite, which was then washed with ethyl acetate, and the filtrate was washed with saturated saline. The organic layer was dried over with anhydrous sodium sulfate, then concentrated. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1) to obtain tert-butyl 5-cyanonicotinate (13.1 g).

المصدر