3-Nitrophthalic anhydride → (Z)-3-(4-fluoro-3-(4-methoxypiperidine-1-carbonyl)benzylidene)-4-nitroisobenzofuran-1(3H)-one

Participants

Reaction Conditions

Reaction Steps

Sodium acetate (6.97 mg, 0.08 mmol) was added to 4-nitroisobenzofuran-1,3-dione (558 mg, 2.89 mmol) and 2-(4-fluoro-3-(4-methoxypiperidine-1-carbonyl)phenyl)acetic acid (43) (502 mg, 1.70 mmol) under air. The resulting mixture was stirred at 240° C. for 30 minutes. The cooled mixture was purified by flash silica chromatography, elution gradient 0 to 100% ethyl acetate in isohexane. Pure fractions were evaporated to dryness to afford the desired material as a yellow gum (50 mg, 6.90% yield); 1H NMR (400.132 MHz, CDCl3) δ 1.59-2.00 (4H, m), 3.10-3.26 (1H, m), 3.37 (3H, s), 3.43-3.57 (2H, m), 3.61-3.71 (1H, m), 3.88-4.05 (1H, m), 7.16-7.20 (1H, m), 7.30 (1H, s), 7.70-7.76 (1H, m), 7.86-7.88 (1H, m), 7.97-8.01 (1H, m), 8.27 (1H, d), 8.39 (1H, d); m/z (LC-MS, ESI+), RT=2.29 (M+H 427.3).

Provenance & Evidence