Sodium Carbonate → HCID 118046170, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N-benzyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (150 mg, 0.445 mmol), 3-chloropyrazin-2-amine (74.9 mg, 0.578 mmol), and PdCl2(dppf)-CH2Cl2 adduct (36.3 mg, 0.044 mmol) in DME (3.3 mL) was added 2 M Na2CO3 (1.11 mL). The reaction mixture was heated at microwave synthesizer (120° C., 10 min). Diluted with EtOAc and washed with water twice. Then extracted with 1N HCl (3×15 mL). The acidic solution was washed with ether twice (2×15 mL), and then basified with Na2CO3. Followed by extracting with EtOAc (20 mL, 3 times) and then washed by sat NaHCO3, water and brine, dried over Na2SO4 and filtered off, concentrated. The crude product was purified with flash chromatography eluting with 0-100% of EtOAc(containing 10% MeOH) in heptane, then concentrated on rotavap. The residue was triturated with ether to provide 80.2 mg of desired product. LCMS (m/z): 305.2 (MH+), 0.59 min. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.74 (d, J=8.22 Hz, 1H) 8.41 (s, 1H) 8.06 (dd, J=9.39, 2.74 Hz, 1H) 8.01 (d, J=8.61 Hz, 2H) 7.94 (br. s., 1H) 7.83 (d, J=8.22 Hz, 2H) 7.40-7.34 (m, 2H) 7.30 (t, J=7.63 Hz, 2H) 7.22 (d, J=7.43 Hz, 1H) 6.40 (d, J=9.39 Hz, 1H) 5.12-5.03 (m, 1H) 3.75-3.60 (m, 2H).

Provenance & Evidence