2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → (9H-fluoren-9-yl)methyl 2-((3-(4-(2-hydroxypropan-2-yl)phenyl)-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)methoxy)ethylcarbamate

Participants

Reaction Steps

To a solution of (9H-fluoren-9-yl)methyl 2-((3-(4-(2-(4-methoxybenzyloxy)propan-2-yl)phenyl)-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)methoxy)ethylcarbamate (0.077 g, 0.089 mmol, prepared using AF from Example #2, Step B cyano intermediate with ((4-(2-(4-methoxybenzyloxy)propan-2-yl)phenyl)magnesium bromide [NOVEL], AG, J.1 with 2-(2-(((9H-fluoren-9-yl)methoxy)carbonylamino)ethoxy)acetic acid [Chem Impex] and L.1 with mercury(II) trifluoroacetate) in DCM (0.94 mL) and Water (0.05 mL) was added DDQ (0.030 gg, 0.134 mmol). The mixture was stirred at rt for about 45 min. The mixture was directly purified by flash chromatography (12 g silica gel column, 35 to 100% EtOAc/heptane) to give (9H-fluoren-9-yl)methyl 2-((3-(4-(2-hydroxypropan-2-yl)phenyl)-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)methoxy)ethylcarbamate (0.03 g, 45%): LC/MS (Table 2, Method b) Rt=2.90 min.; MS m/z: 742 (M+H)+.

Provenance & Evidence