1,4-Dioxane → HCID 67345312, compound

Participants

Reaction Conditions

Reaction Steps

A round-bottomed flask was charged with 3-fluoro-4-(2-iodothieno[3,2-b]pyridin-7-yloxy)benzenamine (Example 6, Step A; 0.600 g, 1.55 mmol), 1-methyl-4-((5-(tributylstannyl)furan-2-yl)methyl)piperazine (0.802 g, 1.71 mmol), PdCl2(PPh3)2 (0.050 g, 0.075 mmol), and dioxane (8 mL). The reaction mixture was heated to 90° C. for 18 hours under nitrogen and then cooled to room temperature. The reaction mixture was diluted with brine (100 mL) and extracted with EtOAc (100 mL). The combined organic layers were dried over sodium sulfate, filter and concentrated. The residue was purified by Biotage 40S eluting with CHCl3/MeOH saturated NH3. (95:5) to provide 430 mg (60%) of the product as a light green solid. 1H NMR (CDCl3, 400 MHz). δ 8.43 (d, J=5.5 Hz, 1H), 7.62 (s, 1H), 7.03 (t, J=8.6 Hz, 1H), 6.69 (d, J=3.5 Hz, 1H), 6.48 (m, 3H), 6.34 (d, J=3.1 Hz, 1H), 3.88 (s, 2H), 3.66 (s, 2H), 2.61 (m, 8H), 2.29 (s, 3H).

Provenance & Evidence