Реакция #798446

Уравнение реакции

tert-butyl (2-oxo-1,2-dihydropyridin-4-yl)methylcarbamate

K2CO3

4-bromo-2-(trifluoromethyl)pyridine

(1R,2R)—N1,N2-dimethylcyclohexane-1,2-diamine

→

tert-butyl (2-oxo-1-(2-(trifluoromethyl)pyridin-4-yl)-1,2-dihydropyridin-4-yl)methylcarbamate

Растворители

ethyl acetate

toluene

Условия реакции

Обработка

1. 1
   workup.ADDITIONTo a reaction vessel containing a stir bar
2. 2
   ДругоеThe reaction vessel was evacuated
3. 3
   Другое110° C. overnight
4. 4
   Фильтрацияfiltered through celite pad
5. 5
   Другоеto remove salt
6. 6
   ДругоеThe filtrate was dried
7. 7
   Другоеthe residue was purified by silica gel flash chromatography
8. 8
   Промывкаeluted with 50% ethyl acetate

Методика

To a reaction vessel containing a stir bar was charged with tert-butyl (2-oxo-1,2-dihydropyridin-4-yl)methylcarbamate 56-4 (72 mg, 0.32 mmol), CuI (12 mg, 0.06 mmol), and K2CO3 (88 mg, 0.64 mmol). The reaction vessel was evacuated and backfilled with nitrogen. A solution of 4-bromo-2-(trifluoromethyl)pyridine 56-5 (94 mg, 0.42 mmol) and (1R,2R)—N1,N2-dimethylcyclohexane-1,2-diamine (9 mg, 0.06 mmol) in toluene (3 mL) was added via syringe. The reaction was stirred at room temperature for 20 minutes, then 110° C. overnight. The reaction mixture was diluted into ethyl acetate and filtered through celite pad to remove salt. The filtrate was dried and the residue was purified by silica gel flash chromatography, and eluted with 50% ethyl acetate to give tert-butyl (2-oxo-1-(2-(trifluoromethyl)pyridin-4-yl)-1,2-dihydropyridin-4-yl)methylcarbamate 56-6. MS m/z 370.2 (M+1).

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