Sodium Carbonate → HCID 57933069, compound

Participants

Reaction Steps

To a 100 mL round bottom flask containing 4-methyl 3-thiophene boronic acid (0.27 g, 1.91 mmol), and 8-(1-ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.65 g, 1.91 mmol) in 20 mL of a stock solution (DME:H2O:EtOH=7:3:2) is added 2 M Na2CO3 (1.9 mL). The resulting mixture is degassed by bubbling N2 for 5 min. Then Pd(PPh3)4 (0.11 g, 0.096 mmol) is added. The reaction mixture is refluxed overnight. The reaction is diluted with H2O (20 mL); extracted with EtOAc (3×30 mL); dried (Na2SO4), filtered and purification of the crude material by chromatography gives the title compound (0.52 g, 1.66 mmol, 87%). 1H NMR (CDCl3): δ 0.89 (t, J=7.5 Hz, 6H), 1.75-1.90 (m, 4H), 2.13 (d, J=0.8 Hz, 3H), 2.44 (s, 3H), 2.49 (s, 3H), 3.30-3.39 (m, 1H), 6.64 (s, 1H), 7.08-7.11 (m, 1H), 7.34 (d, J=3.1 Hz, 1H). ES-MS (m/z): calcd for C18H23N3S (M+H)+: 314.5; found: 314.2.

Provenance & Evidence