2-Fluoro-4-nitrophenol → (7-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)(4-methylpiperazin-1-yl)methanone

Participants

Reaction Conditions

Reaction Steps

MgSO4 (1.41 g, 11.78 mmol) was added to a suspension of 436 (1.16 g, 3.93 mmol), 2-fluoro-4-nitrophenol (1.23 g, 7.85 mmol) and Na2CO3 (1.24 g, 11.78 mmol) in Ph2O (10 mL). The suspension was heated at 160° C. for 1.5 h and at 190° C. for 2 h. After cooling to room temperature, DCM (30 mL) was added and the reaction mixture was filtered and concentrated. The residue was purified by biotage (SNAP 25 g cartridge; AcOEt/Hexane:10/90 over 5 CV then MeOH/DCM: 0/100 to 10/90 over 20CV), to afford the title compound 437 (1.20 g, 2.88 mmol, 73% yield) as a yellow solid. MS (m/z): 417.2 (M+H).

Provenance & Evidence