Dimethyl 4-(4,5-Dimethoxy-2-(methoxymethoxy)phenyl)-5-(3,4-dimethoxyphenyl)-1,2-diazine-3,6-dicarboxylate → Dimethyl 3-(4,5-Dimethoxy-2-(methoxymethoxy)phenyl)-4-(3,4-dimethoxyphenyl)pyrrole-2,5-dicarboxylate

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Reaction Steps

A solution of 7 (1.01 g, 1.91 mmol, 1.0 equiv) in HOAc (25 mL) under Ar at 25° C. was treated with activated Zn dust (1.25 g, 19.1 mmol, 10 equiv), stirred for 4 h, and then treated with additional Zn dust (1.25 g, 10 equiv). After 14.5 h, the slurry was diluted with 10% MeOH/CHCl3 (25 mL) and stirred 3 h at 25° C. The mixture was filtered through Celite, rinsed with 10% MeOH/CHCl3, and the filtrate was washed with saturated aqueous NaHCO3, dried (Na2SO4), and concentrated in vacuo. Chromatography (SiO2, 4.5×15 cm, 25% EtOAc/CH2Cl2) afforded 8 (0.61 g, 62% yield) as an orange oil. An analytically pure sample could be prepared by recrystallization from EtOAc-hexanes: mp 162-163° C.; MALDIHRMS (DHB) m/z 515.1800 (M+, C26H29NO10 requires 515.1791).

Provenance & Evidence