Acetic Acid → HCID 68182975, compound

Participants

Reaction Conditions

Reaction Steps

A dry 40 mL vial charged with a mixture of potassium tert-butoxide (0.110 g, 0.984 mmol) in anhydrous N,N-dimethylformamide (2.0 mL) was cooled to −50° C. with an acetonitrile-dry ice bath under nitrogen. To the vial was added a suspension of ethyl 4-cyano-5-morpholin-4-yl-3-(2-naphthylmethyl)thiophene-2-carboxylate (0.200 g, 0.492 mmol) in anhydrous N,N-dimethylformamide (2.0 mL) dropwise. After 10 min of stirring the resulting black solution, a solution of N-bromomethylphthalimide (0.142 g, 0.590 mmol) in anhydrous N,N-dimethylformamide (1.0 mL) was added dropwise and the mixture was stirred at −52° C.˜−45° C. for 90 min. The reaction was quenched with acetic acid (0.084 mL, 1.5 mmol) and warmed up to r.t. The solution was diluted with water (˜30 mL), and the resulting pale yellow solid was collected by filtration. The crude solid was dissolved in DCM (30 mL), washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated. Purification on a silica gel column (continuous gradient of EtOAc/hexane 0˜50%) afforded the title product (0.126 g, yield 45.3%). LCMS: (FA) ES+ 566. 1H NMR (400 MHz, d-chloroform) δ: 7.95 (s, 1H), 7.90-7.75 (m, 5H), 7.73-7.63 (m, 2H), 7.50-7.40 (m, 3H), 6.03 (m, 1H), 4.87-4.73 (m, 2H), 4.20-4.10 (m, 2H), 3.82-3.75 (m, 4H), 3.51-3.42 (m, 4H), 1.20-1.13 (m, 3H).

Provenance & Evidence