1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → tert-butyl 2-(4-(5-bromo-3-(nicotinamido)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-2-oxoethylcarbamate

Participants

Reaction Steps

The above NMP solution of N-(5-bromo-4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)nicotinamide (0.200 g, 0.498 mmol), 2-(tert-butoxycarbonylamino)acetic acid (0.114 g, 0.648 mmol), HOBT-H2O (0.107 g, 0.698 mmol), and EDCI (0.124 g, 0.648 mmol) were placed in DCM (3 mL). DIEA (d 0.742; 0.434 mL, 2.49 mmol) was then added, and the reaction was stirred at room temperature for 4 hours. The reaction was then quenched with saturated Na2CO3 and extracted into DCM. The organic fractions were combined, dried, filtered, and concentrated to give the crude residue. Purification by column chromatography (500:15 to 500:25 DCM:MeOH) gave tert-butyl 2-(4-(5-bromo-3-(nicotinamido)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-2-oxoethylcarbamate (0.112 g, 40.2% yield).

Provenance & Evidence