Sodium Carbonate → HCID 57585107, compound

Participants

Reaction Steps

To a 5 ml CEM microwave tube was added 2-acetamidobenzo[d]thiazol-6-ylboronic acid (0.1 g, 0.4 mmol), 1-(2-(5-bromopyridin-3-yloxy)ethyl)pyrrolidin-2-one (0.2 g, 0.6 mmol), sodium carbonate (0.6 ml, 1 mmol), Pd FibreCat® (Anchored homogeneous catalyst, Johnson Matthey, West Deptford, N.J. (30% wt, 45 mg), and dioxane (3 mL). The vial was sealed and placed into CEM microwave for 20 min. at 100° C., with 100 watts of power via Powermax®. The reaction mixture was partitioned between EtOAc/water. The aqueous layer was extracted with EtOAc (2×10 mL). The combined organic layers were washed with water, brine, dried over MgSO4 and removed solvent. The crude product was purified using SiO2 chromatography with DCM:MeOH (95%:5%) solvent system to afford the product as white solid. Wt: 45.0 mg. MS (ESI pos. ion) m/z: 397.3. Calc'd exact mass for C20H20N4O3S: 396.46. 1H NMR (300 MHz, chloroform-d) δ ppm 1.99-2.14 (m, 2H) 2.33 (s, 3H) 2.42 (t, J=8.11 Hz, 2H) 3.62 (t, J=7.09 Hz, 2H) 3.74 (t, J=5.19 Hz, 2H) 4.25 (t, J=5.19 Hz, 2H) 7.43 (d, J=2.48 Hz, 1H) 7.62 (dd, J=8.48, 1.90 Hz, 1H) 7.81 (d, J=8.33 Hz, 1H) 7.99 (d, J=1.46 Hz, 1H) 8.27 (d, J=2.63 Hz, 1H) 8.50 (s, 1H).

Provenance & Evidence