Reaktion #166722

Reaktionsgleichung

(S)-tert-Butyl 3-(4-(5-bromo-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-2-(4-chlorophenyl)-3-oxopropyl(isopropyl)carbamate

3,4-dimethoxyphenylboronic acid

K2CO3

→

(S)-tert-butyl 2-(4-chlorophenyl)-3-(4-(5-(3,4-dimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-3-oxopropyl(isopropyl)carbamate

Ausbeute 18.3%

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigedegassed solution of 2:1 toluene
2. 2
   TemperaturThe reaction was then cooled to room temperature
3. 3
   workup.ADDITIONdiluted with water
4. 4
   Extraktionextracted with DCM
5. 5
   SonstigeThe organic fractions were dried
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated
8. 8
   Sonstigepurified (500:10-500:15)

Vorschrift

(S)-tert-Butyl 3-(4-(5-bromo-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-2-(4-chlorophenyl)-3-oxopropyl(isopropyl)carbamate (0.100 g, 0.165 mmol, see Example 4), 3,4-dimethoxyphenylboronic acid (0.0361 g, 0.198 mmol), Pd(PPh3)4 (0.009 g, 0.0083 mmol) and 10% K2CO3 (aq., 0.344 mL, 0.248 mmol) were added to an Ar degassed solution of 2:1 toluene:EtOH (3 mL). The reaction was then heated to 80° C. for 24 hours. The reaction was then cooled to room temperature, diluted with water, and extracted with DCM. The organic fractions were dried, filtered, concentrated, and purified (500:10-500:15) to give (S)-tert-butyl 2-(4-chlorophenyl)-3-(4-(5-(3,4-dimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-3-oxopropyl(isopropyl)carbamate (0.020 g, 18.2% yield).

Quelle