Water → HCID 59198429, compound

Participants

Reaction Steps

To a stirred solution of 8-fluoro-2,5-dihydro-1H-pyrido[4,3-b]indol-1-one (46 g, 228 mmol) in DMF (370 mL) was added NBS (44.5 g, 250 mmol) in small portions at 0° C. The reaction mixture was covered with aluminum foil and left to stir at room temperature overnight. The reaction mixture was treated with water (460 mL), left to stir for 3 h, filtered, and washed with water. The cake was dissolved in MeOH and filtered to remove residual solids. The filtrate was treated with charcoal, and warmed to 40° C. for 2 h. The mixture was cooled to room temperature, filtered through a pad of Celite, and concentrated. The residue was treated with isopropanol and heptane, filtered, and washed with MTBE to afford the title compound as the isopropanol solvate. 1H NMR (600 MHz, CD3SOCD3) 3 12.03 (s, 1H); 11.47 (s, 1H); 7.71 (dd, 1H); 7.59 (s, 1H); 7.52 (dd, 1H); 7.17 (dt, 1H). LRMS (APCI) calc'd for (C11H6BrFN2O) [M+H]+, 281.0. found 280.9.

Provenance & Evidence