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

Participants

Reaction Steps

5-(2-Fluorophenyl)-4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyri dine (0.034 g, 0.0921 mmol), (S)-3-(tert-butoxycarbonyl(isopropyl)amino)-2-(4-chlorophenyl)propanoic acid (0.0330 g, 0.0967 mmol, see Example H), HOBT-H2O (0.0197 g, 0.129 mmol), and EDCI (0.0229 g, 0.120 mmol) were placed in DCM (5 mL) at room temperature. DIEA (d 0.742; 0.0802 mL, 0.460 mmol) was then added, and the reaction was stirred at room temperature for 5 hours. The reaction was then poured into saturated Na2CO3 and extracted into DCM. The organic fractions were combined, dried, filtered and concentrated to give a crude residue that was purified by column chromatography (500:10 DCM:MeOH) to give tert-butyl (2S)-2-(4-chlorophenyl)-3-(4-(5-(2-fluorophenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-3-oxopropyl(isopropyl)carbamate (0.040 g, 70.0% yield). MS APCI (+) m/z 520 detected.

Provenance & Evidence