Reaktion #798446

Reaktionsgleichung

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

Lösungsmittel

ethyl acetate

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONTo a reaction vessel containing a stir bar
2. 2
   SonstigeThe reaction vessel was evacuated
3. 3
   Sonstige110° C. overnight
4. 4
   Filtrationfiltered through celite pad
5. 5
   Sonstigeto remove salt
6. 6
   SonstigeThe filtrate was dried
7. 7
   Sonstigethe residue was purified by silica gel flash chromatography
8. 8
   Wascheneluted with 50% ethyl acetate

Vorschrift

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).

Quelle