Reaktion #802218

Reaktionsgleichung

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

4-(6-chloropyrazin-2-yl)piperazin-2-one

Cs2CO3

→

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

Lösungsmittel

DME

CHCl3

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigepurged under argon atmosphere for 10 min
2. 2
   Sonstigedegassing
3. 3
   Sonstigepurging under argon for additional 10 min
4. 4
   SonstigeAfter completion of the reaction
5. 5
   Filtrationfiltered through Celite
6. 6
   workup.DISTILLATIONThe solvents were distilled off
7. 7
   Sonstigethe crude material was submitted for flash column purification in neutral alumina using 1% MeOH/CHCl3

Vorschrift

The starting material 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (124) (50 mg, 0.205 mmol, 1 eq) and 4-(6-chloropyrazin-2-yl)piperazin-2-one (132) (33 mg, 0.184 mmol, 0.9 eq) in DME (8 mL) was degassed and purged under argon atmosphere for 10 min. To this reaction mixture was charged Cs2CO3 (133 mg, 0.409 mmol, 2 eq) followed by addition of Pd(dpp)Cl2 (6 mg, 0.00819 mmol, 0.04 eq) and degassing and purging under argon for additional 10 min. The reaction mixture was heated at 100° C. for 12 h in a sealed tube. After completion of the reaction, the reaction mixture was diluted with CHCl3 and filtered through Celite. The solvents were distilled off and the crude material was submitted for flash column purification in neutral alumina using 1% MeOH/CHCl3 to obtain pale yellow solid compound 4-(6-(1H-pyrrolo[2,3-b]pyridin-5-yl)pyrazin-2-yl)piperazin-2-one 133 in 9 mg quantity. The compound 133 was confirmed by 1HNMR and LCMS. 1H NMR (400 MHz, CDCl3) δ: 11.84 (s, 1H), 8.95 (d, J=2.07, 1H), 8.64 (d, J=1.95, 1H), 8.57 (s, 1H), 8.23 (s, 1H), 8.18 (s, 1H, 7.53 (m, J=2.92, 1H), 6.56 (m, J=1.70, 1H), 4.18 (s, 2H), 3.89 (m, J=5.36 2H); MS m/z 294.9 (M+H)+.

Quelle