Reaktion #802225

Reaktionsgleichung

MeOH CHCl3

5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine

4-(6-chloropyrazin-2-yl)morpholine

Cs2CO3

→

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

Ausbeute 22.2%

Lösungsmittel

DMF

chloroform

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigepurged with nitrogen for 10 min
2. 2
   Sonstigethe reaction mixture was purged again for another 10 min
3. 3
   SonstigeThe resulting reaction mixture
4. 4
   Sonstigeunder sealed tube condition
5. 5
   SonstigeAfter completion of the reaction the mass
6. 6
   Filtrationfiltered through Celite
7. 7
   Sonstigethe solvents were removed
8. 8
   Sonstigeto obtain the crude product

Vorschrift

A stirred solution of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (147) (100 mg, 0.4 mmol) and 4-(6-chloropyrazin-2-yl)morpholine (103) (80 mg, 0.4 mmol) in DMF (5 mL) was degassed and purged with nitrogen for 10 min. To this reaction mixture was added Cs2CO3 (333 mg, 1.0 mmol, 2.5 eq) and the reaction mixture was purged again for another 10 min followed by the addition of Pd(PPh3)4 (0.018 mg, 0.016 mmol, 0.04 eq). The resulting reaction mixture was heated to 100° C., overnight under sealed tube condition. After completion of the reaction the mass was diluted with chloroform and filtered through Celite and the solvents were removed to obtain the crude product. The crude was passed through neutral alumina eluting with 2-3% MeOH/CHCl3 provided a white coloured solid 25 mg of 4-(6-(1H-pyrrolo[2,3-b]pyridin-5-yl)pyrazin-2-yl)morpholine 148. 1H NMR (400 MHz, CDCl3) δ: 8.96 (s, 1H), 8.95 (s, 1H), 8.84 (s, 1H), 8.54 (d, J=1.95, 1H), 8.43 (s, 1H), 8.07 (s, H), 7.36 (m, 1H), 3.71 (t, 4H), 3.69 (bt, 4H); MS m/z 281.90 (M+H)+.

Quelle