Tetrahydrofuran → 1-[4-(4-Isobutylamino-imidazo[1,2-a]quinoxalin-1-yl)-phenyl]-3-[4-(4-methyl-piperazin-1-ylmethyl)-3-trifluoromethyl-phenyl]-urea

Participants

Reaction Conditions

Reaction Steps

1-[4-(4-Methyl-piperazin-1-ylmethyl)-3-trifluoromethyl-phenyl]-3-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-urea (244 mg, 0.47 mmol) was dissolved in potassium carbonate (1.41 mL, 1M in water) and THF (1 mL) and stirred overnight at rt in a sealed vial. (1-bromo-imidazo[1,2-a]quinoxalin-4-yl)-isobutyl-amine (75 mg, 0.235 mmol), Pd(OAc)2 (10.6 mg, 0.047 mmol) and P(oTol)3 (28.6 mg, 0.094 mmol) were added and the mixture was heated at 140° C. under microwave irradiation for 40 min. After cooling, the solution was filtered and subjected to preparative HPLC to give 1-[4-(4-isobutylamino-imidazo[1,2-a]quinoxalin-1-yl)-phenyl]-3-[4-(4-methyl-piperazin-1-ylmethyl)-3-trifluoromethyl-phenyl]-urea (24.8 mg, 14%): 1H-NMR (300 MHz, d6-DMSO): δ=9.30 (1H, s), 9.24 (1H, s), 7.98 (1H, s), 7.68-7.50 (6H, m), 7.47 (3H, m), 7.27 (2H, m), 6.93 (1H, dd), 3.51 (2H, s), 3.37 (2H, dd), 2.38 (8H, br s), 2.19 (3H, s), 2.09 (1H, sept), 0.91 (6H, d) ppm; UPLC-MS: RT=1.03 min; m/z (ES+) 631.7 [MH+]; required MW=630.7.

Provenance & Evidence