Diisopropylethylamine → (3aR,7aR)-tert-butyl 4-(6-chloro-5-cyanopyrazin-2-yl)octahydro-1H-pyrrolo[3,2-b]pyridine-1-carboxylate

Participants

Reaction Steps

Commercial (3aR,7aR)-tert-butyl octahydro-1H-pyrrolo[3,2-b]pyridine-1-carboxylate (416, CAS: 1251010-63-5, 476 mg, 2.1 mmol) was dissolved in 15 mL DMF. To it were added 3,5-dichloropyrazine-2-carbonitrile (340 mg, 1.9 mmol) and DIEA (500 μL, 2.9 mmol). The mixture was stirred at RT for 3.5 hours, diluted with 100 mL EtOAc, washed with water ×3, dried, concentrated in vacuo, and subjected to silica flash column using 0 to 3% MeOH in DCM to isolate (3aR,7aR)-tert-butyl 4-(6-chloro-5-cyanopyrazin-2-yl)octahydro-1H-pyrrolo[3,2-b]pyridine-1-carboxylate (417, 670 mg, 88%) as a white solid.

Provenance & Evidence