2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-YL)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-C]pyridin-4-one → 2-(3-(tert-butylamino)-2-((2,4-dimethoxybenzyl)amino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one

Participants

Reaction Conditions

Reaction Steps

A mixture of N3-(tert-butyl)-N2-(2,4-dimethoxybenzyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoxaline-2,3-diamine (304c; 109.6 mg, 0.09 mmol), 2-bromo-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (608) (80 mg, 0.37 mmol), K2PO4 (59 mg, 0.28 mmol), X-Phos (Strem Chemicals, Inc.) (4.46 mg, 9.35 μmol), and Pd2dba3 (Aldrich) (4.28 mg, 4.67 μmol) in a mixture of dioxane (1.0 mL) and water (0.20 mL) was stirred under argon at 105° C. for 3 h. Additional Pd2dba3 (4.28 mg, 4.67 μmol) and dicyclohexyl(2′,4′,6′-triisopropyl-[1,1′-biphenyl]-2-yl)phosphine (4.46 mg, 9.35 μmol) were added, and the resulting mixture was stirred under argon at 105° C. for 15 h. The reaction mixture was subsequently diluted with DCM (10 mL) and concentrated onto silica gel. Chromatographic purification (silica gel, 0-100% EtOAc/hexanes, then 0-10% MeOH/DCM) furnished 2-(3-(tert-butylamino)-2-((2,4-dimethoxybenzyl)amino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (56.3 mg) as a yellow solid: m/z (ESI, +ve) 501.2 (M+H)+.

Provenance & Evidence