反应详情

温度

23 °C

Dimethyl(1-diazo-2-oxopropyl)phosphonate (Anichem, Inc., North Brunswick, N.J.; 8.63 μl, 0.06 mmol) was added to a suspension of 3-(tert-butylamino)-5-(4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridin-2-yl)quinoxaline-2-carbaldehyde (307b) (19.0 mg, 0.05 mmol) and K2CO3 (28.9 mg, 0.21 mmol) in MeOH (1.0 mL) and the resulting mixture was stirred at 23° C. for 16 h. Additional dimethyl(1-diazo-2-oxopropyl)phosphonate (20 μl, 0.13 mmol) was added, and the resulting mixture was stirred at 23° C. for 17 h. The reaction mixture was subsequently 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-ethynylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (2.8 mg, 7.79 μmol, 15% yield) as a yellow solid (following trituration with Et2O (0.5 mL)): 1H NMR (400 MHz, CDCl3) δ ppm 12.39 (1H, br. s.), 8.14 (1H, d, J=7.4 Hz), 8.10 (1H, d, J=8.0 Hz), 8.04 (1H, d, J=3.9 Hz), 7.72 (1H, t, J=7.8 Hz), 6.82 (1H, d, J=3.7 Hz), 5.49 (1H, br. s.), 3.81-3.86 (1H, m), 3.68-3.75 (2H, m), 3.06 (2H, t, J=6.9 Hz), 1.96 (9H, s). m/z (ESI, +ve) 360.2 (M+H)+.

1. stirringthe resulting mixture was stirred at 23° C. for 17 h
2. concentrationThe reaction mixture was subsequently concentrated onto silica gel
3. customchromatographically purified (silica gel, 0-100% EtOAc/hexanes