Sodium Carbonate → (R)-tert-Butyl 3-(4-chlorophenyl)-1-(4-(3-methyl-5-phenyl-1H-pyrrolo [2,3-b]pyridin-4-yl)piperazin-1-yl)-1-oxopropan-2-ylcarbamate

Participants

Reaction Steps

3-Methyl-5-phenyl-4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine (0.050 g, 0.14 mmol, see Example 15), (R)-2-(tert-butoxycarbonylamino)-3-(4-chlorophenyl)propanoic acid (0.0451 g, 0.151 mmol), HOBT-H2O (0.0293 g, 0.192 mmol) and EDCI (0.0341 g, 0.178 mmol) were placed in DCM (5 mL) at room temperature. DIEA (d 0.742; 0.119 mL, 0.684 mmol) was then added, and the reaction was stirred for 5 hours. The reaction was then poured into saturated Na2CO3 and extracted into DCM. The reaction was then dried, filtered, concentrated, and purified (500:5 DCM:MeOH) to give (R)-tert-butyl 3-(4-chlorophenyl)-1-(4-(3-methyl-5-phenyl-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-1-oxopropan-2-ylcarbamate (0.030 g, 38.1% yield).

Provenance & Evidence