Water → HCID 71599639, compound

Participants

Reaction Conditions

Reaction Steps

To the mixture of 4-(4-bromo-2-methyl-1H-benzo[d]imidazol-6-yl)morpholine (0.8 g, 2.70 mmol) in N,N-Dimethylformamide (DMF) (10 mL) was added 7-(bromomethyl)benzo[b]thiophene (0.920 g, 4.05 mmol)) and potassium carbonate (1.120 g, 8.10 mmol). The resulting reaction mixture was stirred at 90° C. for 2 h, then more 7-(bromomethyl)benzo[b]thiophene (0.920 g, 4.05 mmol) was added in and the reaction mixture was stirred at 100° C. for 4 h. It was cooled to room temperature and poured into water (100 mL). The aqueous mixture was extracted with DCM (100 mL×2). The combined organic phase was washed with Brine (100 mL) and concentrated. The crude material was purified on silica column (20˜90% EtOAc in Hexane) to give the product as solid (0.69 g, 58% %). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.42 (s, 3H) 2.95-3.07 (m, 4H) 3.66-3.72 (m, 4H) 5.69 (s, 2H) 6.81 (d, J=7.07 Hz, 1H) 7.00 (d, J=2.02 Hz, 1H) 7.09 (d, J=2.02 Hz, 1H) 7.36 (t, J=7.58 Hz, 1H) 7.53 (d, J=5.56 Hz, 1H) 7.79 (d, J=5.56 Hz, 1H) 7.85 (d, J=7.65 Hz, 1H); MS (ES+) m/e 442.0 [M+H]+.

Provenance & Evidence