Potassium Carbonate → 4-{2-Methoxy-4-[3-(2-morpholin-4-yl-ethyl)-2,4-dioxo-thiazolidin-5-ylidenemethyl]-phenoxy}-3-trifluoromethyl-benzonitrile

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Reaction Steps

A solution of 4-[4-(2,4-Dioxo-thiazolidin-5-ylidenemethyl)-2-methoxy-phenoxy]-3-trifluoromethyl-benzonitrile (40 mg, 0.095 mmol) and 4-(2-Chloro-ethyl)-morpholine (0.095 mmol) in DMF (1.5 mL) was treated with K2CO3 (33 mg, 0.24 mmol) and heated to 80° C. in an aluminum heating block. After 12 h, the reaction was cooled to RT and partitioned between EtOAc (5 mL) and H2O (5 mL). The organic phase was washed with H2O (2×5 mL), dried over Na2SO4 and concentrated in vacuo. Silica gel chromatography (MeOH/CH2Cl2) afforded the title compound. 1H NMR (400 Hz, CDCl3) δ 7.97 (d, 1H), 7.87 (s, 1H), 7.68 (dd, 1H), 7.19 (m, 3H), 6.76 (d, 1H), 3.90 (t, 2H), 3.82 (s, 3H), 3.67 (bs, 4H), 2.64 (t, 2H), 2.51 (bs, 4H); LC/MS (m/z) [M+1]+ 534.2 (calculated for C25H23F3N3O5S, 534.12).

Provenance & Evidence