Reaktion #1588014

Reaktionsgleichung

Lithium chloride

5-bromo-1H-pyrrolo[2,3-b]pyridin-2(3H)-one

(3-acrylamidophenyl)boronic acid

N-(3-(3-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)pent-2-ynamide

sodium carbonate

→

N-(3-(2-oxo-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)acrylamide

Lösungsmittel

toluene ethanol water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction was degassed
2. 2
   Sonstigepurged nitrogen for 10 min
3. 3
   SonstigeThe reaction was degassed
4. 4
   Sonstigepurged with nitrogen for another 10 min
5. 5
   Sonstigeunder sealed condition for overnight
6. 6
   Temperaturto cool to room temperature
7. 7
   workup.ADDITIONdiluted with chloroform
8. 8
   FiltrationThe organic layer was filtered through celite plug
9. 9
   Einengenconcentrated
10. 10
    Sonstigeto get the crude
11. 11
    SonstigeThe crude was purified through flash chromatography
12. 12
    WaschenThe compound was eluted in ethyl acetate in hexane as half white solid N-(3-(2-oxo-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)acrylamide 150

Vorschrift

A solution of 5-bromo-1H-pyrrolo[2,3-b]pyridin-2(3H)-one 149 (100 mg, 0.4673 mmol) and (3-acrylamidophenyl)boronic acid 64 (98.55 mg, 0.514 mmol) in toluene/ethanol/water was added sodium carbonate (198 mg, 1.8692 mmol). Lithium chloride (59.3 mg, 1.40 mmol) was added to the reaction. The reaction was degassed and purged nitrogen for 10 min. Pd(dppf)Cl2 (19.03 mg, 0.0233 mmol) was added to the reaction. The reaction was degassed and purged with nitrogen for another 10 min. The reaction was heated to 90° C. under sealed condition for overnight. The reaction mixture was allowed to cool to room temperature, diluted with chloroform. The organic layer was filtered through celite plug and concentrated to get the crude. The crude was purified through flash chromatography by using 100-200 mesh silica gel. The compound was eluted in ethyl acetate in hexane as half white solid N-(3-(2-oxo-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)acrylamide 150. MS-ES+338.9, 1H NMR (400 MHz, DMSO): 11.09 (s, 1H), 10.24 (s, 1H), 8.30 (s, 1H), 7.97 (s, 1H), 7.61 (d, 1H), 7.35 (m, 2H), 6.44 (m, 1H), 6.25 (d, 1H), 5.76 (d, 1H), 3.63 (s, 2H).

Quelle