Potassium Carbonate → HCID 57826940, compound

Participants

Reaction Steps

To a solution of tert-butyl 3-bromothiophen-2-ylcarbamate (1 g, 3.59 mmol) in DMF (15 mL) was added K2CO3 (1.987 g, 14.38 mmol) and (E)-methyl 4-bromopent-2-enoate (prepared according to C. Girard et al, TL, vol 30, No. 52, pp 7399-7402, 1989) (1.388 g, 7.19 mmol). The reaction mixture was stirred at ambient temperature for 16 h. Palladium(II) acetate (0.040 g, 0.180 mmol) and PPh3 (0.094 g, 0.359 mmol) were added and the reaction mixture was heated to 85° C. for 18 h. DCM was added and the resulting solution was washed with water. The layers were separated and the organic solution was dried over MgSO4, filtered, and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel (heptane/EtOAc: 95/5 to 55/45) to give the title compound (0.404 g, 36.3%): LC/MS (Table 1, Method d) Rt=2.40 min; MS m/z 310 (M+H)+; 1H NMR (CDCl3) δ 6.97 (m, 2H), 3.72 (s, 3H), 3.62 (s, 2H), 2.56 (s, 3H), 1.70 (s, 9H).

Provenance & Evidence