Sodium Carbonate → Tert-butyl 3-(4-chlorobenzyl)-4-(4-(3-methyl-5-phenyl-1h-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-4-oxobutylcarbamate

Participants

Reaction Steps

3-Methyl-5-phenyl-4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine (0.050 g, 0.137 mmol, see Example 15), 4-(tert-butoxycarbonylamino)-2-(4-chlorobenzyl)butanoic acid (0.0494 g, 0.151 mmol), HOBT-H2O (0.0293 g, 0.192 mmol), and EDCI (0.0341 g, 0.178 mmol) were placed in DCM (3 mL) at room temperature. DIEA (d=0.742; 0.119 mL, 0.684 mmol) was then added, and the reaction was stirred at room temperature for 15 hours. The reaction was then poured into saturated Na2CO3 and extracted with DCM. The combined organic fractions were dried, filtered, concentrated, and purified (500:5 DCM:MeOH) to give tert-butyl 3-(4-chlorobenzyl)-4-(4-(3-methyl-5-phenyl-1H-pyrrolo[2,3-b]pyri din-4-yl)piperazin-1-yl)-4-oxobutylcarbamate (0.010 g, 12.1% yield).

Provenance & Evidence