Hydrochloric Acid → HCID 71251917, compound

Participants

Reaction Steps

To a solution of INTERMEDIATE 9 HCl salt (72.4 mg, 0.17 mmol) in DMF (1.0 ml) was added 2-bromoacetophenone (83.0 mg, 0.42 mmol), followed by the portionwise addition of potassium carbonate (138.0 mg, 1.00 mmol). After stirring at ambient temperature overnight, the reaction mixture was quenched with a saturated solution of ammonium chloride, extracted with EtOAc, and washed with water and brine. The organic layer was separated, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified using a silica gel cartridge using a gradient of 0-50% ethyl acetate in hexanes, followed by a gradient of 0-10% methanol in dichloromethane to give the title compound as a yellow oil, which solidified on standing. LC-MS (m/z): 443.10 [M+H]+. 1H NMR (CDCl3, 500 MHz): δ 8.92 (d, J=4.8 Hz, 2H), 8.25-8.27 (in, 2H), 8.10 (d, J=8.1 Hz, 2H), 7.60-7.62 (m, 1H), 7.50 (t, J=7.6 Hz, 2H), 7.37 (t, J=4.8 Hz, 1H), 7.15 (t, J=8.6 Hz, 2H), 3.88 (s, 2H), 3.80-3.86 (in, 1H), 3.13-3.15 (br, 2H), 2.41-2.45 (br, 2H), 2.07-2.27 (br, 4H).

Provenance & Evidence