Reaktion #802217

Reaktionsgleichung

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

1-(6-bromopyrazin-2-yl)pyrrolidin-2-one

→

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

Lösungsmittel

CHCl3

DME

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

To 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 1-(6-bromopyrazin-2-yl)pyrrolidin-2-one (46) (49 mg, 0.205 mmol, 1 eq) in DME (5 mL), was added Pd(PPh3)4 (7.1 mg, 0.00614 mmol, 0.02 eq) Cs2CO3 (133 mg, 0.410 mmol, 2 eq) and degassing and purging under argon for additional 10 min was performed. 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 1-(6-(1H-pyrrolo[2,3-b]pyridin-5-yl)pyrazin-2-yl)pyrrolidin-2-one 131 in 9 mg quantity. The compound 131 was confirmed by 1HNMR and LCMS. 1H NMR (400 MHz, CDCl3) δ: 11.90 (s, 1H), 9.46 (s, 1H), 9.02 (d, J=10.48, 2H), 8.71 (s, 1H), 7.56 (s, 1H), 6.58 (s, 1H)], 4.13 (m, J=7.07, 2H), 2.65 (m, J=8.04, 2H), 2.14 (m, J=192.19, 2H); MS m/z 279.9 (M+H)+.

Quelle