tert-Butyl carbazate → HCID 58382419, compound

Participants

Reaction Conditions

Reaction Steps

To a flask was added Pd2 dba3 (0.309 g, 0.338 mmol), tert-Butyl X-Phos (0.287 g, 0.676 mmol) and 1,4-dioxane (25 mL). The mixture was heated to about 80° C. for about 10 min and then 2-bromo-6-(1-methyl-1H-pyrazol-4-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine (1.38 g, 3.38 mmol, prepared using B from Preparation #A.1 and C), tert-butyl hydrazinecarboxylate (0.670 g, 5.07 mmol) and NaOt-Bu (0.487 g, 5.07 mmol) were then added and mixture was heated at about 80° C. for about 1 h. The mixture was cooled, filtered through Celite® and the filter pad was rinsed with EtOAc. The filtrate was concentrated in vacuo then purified by flash chromatography (40 g silica column eluting with 0 to 100% EtOAc/DCM to provide tert-butyl 2-(6-(1-methyl-1H-pyrazol-4-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)hydrazinecarboxylate (0.510 g, 33%): LC/MS (Table 2, Method c) Rt=1.59 min; MS m/z 460 (M+H)+.

Provenance & Evidence