2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → 2-(3-(tert-butylamino)-2-ethylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 8-bromo-N-(tert-butyl)-3-ethylquinoxalin-2-amine (312b; 134.8 mg, 0.437 mmol), 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (609) (345 mg, 0.90 mmol), K2PO4 (279 mg, 1.31 mmol), X-Phos (Strem Chemicals, Inc.) (20 mg, 0.04 mmol), and Pd2dba3 (Aldrich, 20 mg, 0.022 mmol) in a mixture of 1,4-dioxane (5.0 mL) and water (1.00 mL) was stirred under argon at 100° C. for 1 h. The reaction mixture was then concentrated onto silica gel and chromatographically purified (silica gel, 0-100% EtOAc/hexanes, then 0-10% MeOH/DCM) to provide 2-(3-(tert-butylamino)-2-ethylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (6.7 mg, 0.018 mmol, 4% yield) as a yellow-orange solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.00 (1H, br. s.), 7.82 (1H, dd, J=7.4, 1.2 Hz), 7.60 (1H, dd, J=8.1, 1.3 Hz), 7.33 (1H, t, J=7.8 Hz), 7.02 (1H, d, J=2.0 Hz), 6.96 (1H, br. s.), 6.04 (1H, s), 3.42 (2H, td, J=6.9, 2.2 Hz), 2.90 (2H, q, J=7.2 Hz), 2.85 (2H, t, J=7.0 Hz), 1.56 (9H, s), 1.29 (3H, t, J=7.2 Hz). m/z (ESI, +ve) 364.1 (M+H)+.

Provenance & Evidence