Hydrochloric Acid → HCID 59842996, compound

Participants

Reaction Conditions

Reaction Steps

To a 4 mL microwave tube was added 4-(2-(2-fluoro-5-(4-methylthiophen-2-yl)pyridin-3-yl)ethoxy)-7-methoxyquinoline (0.025 g, 0.063 mmol), aq. HCl (5N, 2 mL), and dioxane (3 mL). The resulting mixture was sealed and heated to reflux (105° C.) in closed system for 20 h. The reaction mixture was partitioned between EtOAc/satd. NaHCO3. The aqueous layer was extracted with EtOAc and the combined organic layers were dried over MgSO4 and concentrated. The crude product was purified using SiO2 chromatography with CH2Cl2:EtOAc:MeOH (2M NH3) (90%:6%:4%) to afford the product as whit solid (15 mg). MS (ESI pos. ion) m/z (MH+): 393.3. Calc'd exact mass for C22H20N2O3S: 392.1. 1H NMR (300 MHz, MeOH-d4) δ ppm 2.24 (s, 3 H) 3.20 (t, J=6.28 Hz, 2 H) 3.93 (s, 3 H) 4.54 (t, J=6.28 Hz, 2 H) 6.90 (s, 1 H) 6.94 (d, J=5.55 Hz, 1 H) 6.96 (s, 1 H) 7.11 (dd, J=9.21, 2.48 Hz, 1 H) 7.27 (d, J=2.34 Hz, 1 H) 7.55 (d, J=2.63 Hz, 1 H) 7.88 (d, J=2.48 Hz, 1 H) 8.10 (d, J=9.21 Hz, 1 H) 8.57 (d, J=5.55 Hz, 1 H).

Provenance & Evidence