Step 82a: Synthesis of 1-(4-bromophenyl)pyrrolidine (compound 0601-155)
A mixture of 4-bromoaniline (1 g, 5.81 mmol), Cs2CO3 (5.68 g, 17.44 mmol), and 1,4-dibromobutane (1.88 g, 8.72 mmol) was dissolved in DMF (20 mL), and the reaction was stirred at 60 °C overnight. After completion of the reaction, the mixture was cooled to room temperature, diluted with water (200 mL) and extracted with ethyl acetate (2 x 100 mL). The organic layers were combined, washed sequentially with water (3 x 100 mL) and brine (100 mL) and dried over anhydrous Na2SO4. After concentration under reduced pressure, purified by silica gel column chromatography (eluent: petroleum ether), the target compound 0601-155 (720 mg, 46% yield) was obtained as a colorless oil.LCMS: 226 [M + 1]+.1H NMR (400MHz, DMSO-d6) δ1.94 (t, J=6.4Hz, 4H), 3.18 (t, J=6.4Hz, 4H), 6.18 (t, J=6.4Hz, 4H). Hz, 4H), 6.47 (d, J=9.2Hz, 2H), 7.27 (d, J=9.2Hz, 2H).
