反应详情

温度

105 °C

A mixture of 3-(tert-butylamino)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoxaline-2-carbaldehyde (307a) (600.0 mg, 1.18 mmol), 2-bromo-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (608) (407 mg, 1.89 mmol), K2PO4 (753 mg, 3.55 mmol), X-Phos (Strem Chemicals, Inc., 56.4 mg, 0.12 mmol), and Pd2dba3 (Aldrich, 54.1 mg, 0.06 mmol) in a mixture of 1,4-dioxane (10 mL) and water (2.0 mL) was heated under argon at 105° C. for 1 h. The reaction mixture was cooled to RT, diluted with water (30 mL), and extracted with 5% MeOH/DCM (3×30 mL). The combined extracts were dried over Na2SO4, filtered, and concentrated onto silica gel. Chromatographic purification (silica gel, 0-100% EtOAc/hexanes, then 0-10% MeOH/DCM) furnished 3-(tert-butylamino)-5-(4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridin-2-yl)quinoxaline-2-carbaldehyde (79.0 mg, 0.22 mmol, 18% yield) as a dark-red solid: m/z (ESI, +ve) 364.2 (M+H)+.

1. temperatureThe reaction mixture was cooled to RT
2. extractionextracted with 5% MeOH/DCM (3×30 mL)
3. dry with materialThe combined extracts were dried over Na2SO4
4. filtrationfiltered
5. concentrationconcentrated onto silica gel
6. customChromatographic purification (silica gel, 0-100% EtOAc/hexanes