Potassium Phosphate, Tribasic → 2-(3-(tert-butylamino)-2-methylquinoxalin-5-yl)-1H-pyrrolo[2,3-d]pyridazin-4(5H)-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-bromo-1H-pyrrolo[2,3-d]pyridazin-4(5H)-one (47.0 mg, 0.220 mmol), N-(tert-butyl)-3-methyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoxalin-2-amine (174b; 94 mg, 0.220 mmol), K3PO4 (140 mg, 0.659 mmol), Pd2dba3 (Aldrich; 10.05 mg, 10.98 μmol), and XPhos (Strem Chemicals, Inc., 10.47 mg, 0.022 mmol) in a mixture of dioxane (1.5 mL) and water (0.38 mL) was stirred under argon at 70° C. for 1.5 h. The reaction mixture was subsequently heated at 90° C. for 17 h. The reaction mixture was then concentrated onto silica gel and chromatographically purified (silica gel, 50-100% EtOAc/hexanes, then 0-10% MeOH/DCM) to provide 2-(3-(tert-butylamino)-2-methylquinoxalin-5-yl)-1H-pyrrolo[2,3-d]pyridazin-4(5H)-one (16.8 mg, 0.048 mmol, 22% yield) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.60 (1H, br. s.), 12.24 (1H, s), 8.16 (1H, d, J=0.4 Hz), 7.97 (1H, dd, J=7.4, 1.4 Hz), 7.75 (1H, dd, J=8.0, 1.4 Hz), 7.43 (1H, t, J=7.7 Hz), 7.38 (1H, s), 6.11 (1H, s), 2.58 (3H, s), 1.54 (9H, s). m/z (ESI, +ve) 349.0 (M+H)+.

Provenance & Evidence