Sodium Methoxide → 4-[2-(2,2-Dimethyl-5-oxo-2,5-dihydro-1H-pyrrol-1-yl)-1,3-thiazol-4-yl]benzonitrile

Participants

Reaction Steps

Methyl (2E)-4-{[4-(4-cyanophenyl)-1,3-thiazol-2-yl]amino}-4-methylpent-2-enoate (0.15 g, 0.46 mmol), prepared in the previous step, was dissolved in tetrahydrofuran (2 mL) and sodium methoxide (53 mg, 1.0 mmol) was added. The mixture was stirred for 2 h, quenched with saturated NH4Cl, diluted with ethyl acetate, washed with H2O, brine, dried over anhydrous MgSO4, filtered and concentrated. Flash chromatography (20% acetone/hexane) afforded the title compound (0.105 g, 78%) as a white solid. HRMS: calcd for C16H13N3OS+H+, 296.08521; found (ESI, [M+H]+), 296.0867; Analytical HPLC: purity 99.0% at 210-370 nm, 9.8 min; 97.8% at 304 nm, 9.8 min; the Xterra® RP18 column, 3.5μ, 150×4.6 mm column, 1.2 mL/min, 85/15-5/95 (Ammon. Form. Buff. pH=3.5/ACN+MeOH) for 10 min, hold 4 min.

Provenance & Evidence