Reaktion #1717127

Reaktionsgleichung

4-(6-(1H-pyrrolo[2,3-b]pyridin-5-yl)pyrazin-2-yl)morpholine

dichloromethane

→

4-(6-(3-chloro-1H-pyrrolo[2,3-b]pyridin-5-yl)pyrazin-2-yl)morpholine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe resulting reaction mixture
2. 2
   SonstigeAfter completion of the reaction the solvents
3. 3
   Sonstigewere removed
4. 4
   Extraktionextracted into CH2Cl2
5. 5
   SonstigeThe organic layer was separated
6. 6
   Extraktionthe aqueous phase was extracted with CH2Cl2
7. 7
   WaschenThe combined organic layer was washed with brine solution
8. 8
   Trocknendried over sodium sulphate
9. 9
   Sonstigethe solvents were removed by rotary evaporator
10. 10
    SonstigeThe crude material was purified by flash column with 100-200 mesh silica gel employing 70% EtOAc/hexane eluents

Vorschrift

To a solution of compound 4-(6-(1H-pyrrolo[2,3-b]pyridin-5-yl)pyrazin-2-yl)morpholine (148) (40 mg, 0.142 mmol, 1.0 eq) in dichloromethane (6 mL) was added n-chlorosuccinamide (38 mg, 0.283 mmol, 2.0 eq) and the resulting reaction mixture was stirred at room temperature overnight. After completion of the reaction the solvents were removed and extracted into CH2Cl2. The organic layer was separated and the aqueous phase was extracted with CH2Cl2 to retain the crude material. The combined organic layer was washed with brine solution and dried over sodium sulphate and the solvents were removed by rotary evaporator. The crude material was purified by flash column with 100-200 mesh silica gel employing 70% EtOAc/hexane eluents to obtain the pure off-white colored solid of 4-(6-(3-chloro-1H-pyrrolo[2,3-b]pyridin-5-yl)pyrazin-2-yl)morpholine 149 (10 mg). 1H NMR (400 MHz, CDCl3) δ: 9.0 (s, 1H), 8.83 (s, 1H), 8.52 (s, 1H), 8.45 (s, 1H), 8.10 (s, 1H), 7.34 (d, J=2.31 Hz, 1H), 3.89 (m, 4H), 3.70 (m, 4H); MS m/z 315.9 (M+H)+.

Quelle