تفاعل #41724

معادلة التفاعل

potassium carbonate

tert-butyl 4-chloropyridine-2-carboxylate

KHMDS

4-amino-3-nitrophenol

→

desired product

tert-butyl 4-(4-amino-3-nitrophenoxy)pyridine-2-carboxylate

المذيبات

dimethylformamide

dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   أخرىThe reaction was evaporated under reduced pressure
2. 2
   workup.ADDITIONdiluted with excess ethyl acetate and water
3. 3
   استخلاصAn extraction of the aqueous layer
4. 4
   غسيلwashed 4 times with water
5. 5
   تجفيفThe organic layer was dried over anhydrous sodium sulfate
6. 6
   أخرىevaporated under reduced pressure
7. 7
   أخرىThe crude material was purified by flash silica gel chromatography
8. 8
   workup.ADDITIONan eluent of 1:1 mixture of hexanes to ethyl acetate

الإجراء التجريبي

Solid anhydrous white powdered KHMDS (2 eq) was suspended in a solution of dimethylformamide. Red crystalline 4-amino-3-nitrophenol (1 eq) was charged to the rapidly stirring solution under an inert atmosphere and the heterogeneous solution was allowed to stir for 2 hours. Then a dimethylformamide solution of tert-butyl 4-chloropyridine-2-carboxylate (1 eq) was added dropwise. Anhydrous powdered potassium carbonate (1.2 eq) was charged to the reaction as an acid scavenger. The purple colored viscous mixture was heated to 80° C. for 12-15 hours until when it was determined to be complete by HPLC. The reaction was evaporated under reduced pressure and diluted with excess ethyl acetate and water. An extraction of the aqueous layer was made with ethyl acetate. The organic layers were combined and washed 4 times with water followed by brine. The organic layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The crude material was purified by flash silica gel chromatography using an eluent of 1:1 mixture of hexanes to ethyl acetate to give the desired product. MS: MH+=332.

المصدر