Hydrochloric Acid → HCID 21846684, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 6-[[4-(4-ethylphenyl)-2,2-dimethyl-(2H)-thiochromen-6-yl]-ethynyl]-nicotinate (Compound 241, 110.0 mg, 0.24 mmol) in 3.0 mL THF and 3.0 mL EtOH was added NaOH (120.0 mg, 3.0 mmol, 3.0 mL of a 1M aqueous solution). This mixture was heated to 40° C. for 1 hour, cooled to room temperature, and the resulting solution was stirred overnight. The reaction mixture was acidified with 10% aqueous HCl and extracted with EtOAc. The combined organic layers were washed with H2O, saturated aqueous NaCl, and dried (Na2SO4) before removing the solvent under reduced pressure to give 100 mg (96%) of the title compound as a colorless solid. 1H NMR (300 MHz, d6 -acetone) δ: 9.08 (1H, d, J=2.0 Hz), 8.30 (1H, dd, J=2.2, 8.2 Hz), 7.66 (1H, d, J=8.2 Hz), 7.46 (2H, s), 7.31-7.21 (5H, m), 5.95 (1H, s), 2.69 (2H, q, J=7.6 Hz), 1.48 (6H, s), 1.25 (3H, t, J=7.6 Hz).

Provenance & Evidence