Trifluoroacetic acid → HCID 89783608, compound

Participants

Reaction Steps

A mixture of rac-tert-butyl 7-benzyl-4-oxo-2-(quinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridine-5(4H)-carboxylate (200 mg, 0.441 mmol), DCM (10 mL), and TFA (2 mL) was stirred at RT for 2 h. The mixture was concentrated in vacuo, and the residue was suspended in 1N aq. HCl (10 mL) and washed with EtOAc (5 mL). The aq. layer was neutralized with sat. aq. NaHCO3 (5 mL) and extracted with EtOAc (2×10 mL). The combined extracts were dried over Na2SO4, filtered, and concentrated in vacuo. Purification of the residue by preparative TLC (80% EtOAc/petroleum ether) afforded rac-7-benzyl-2-(quinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (30 mg, 0.085 mmol, 19% yield) as a pale green solid: 1H NMR (400 MHz, DMSO-d6) δ 12.29 (1H, br s), 8.92 (1H, dd, J=1.6 Hz & 2.8 Hz), 8.47 (1H, dd, J=1.6 Hz & 6.8 Hz), 8.21 (1H, d, J=7.2 Hz), 7.86 (1H, d, J=8 Hz), 7.67-7.62 (2H, m), 7.43-7.40 (4H, m), 7.33-7.30 (1H, m), 7.18 (1H, d, J=2 Hz), 7.06 (1H, br s), 3.48-3.40 (1H, m), 3.20-3.10 (2H, m), 2.92-2.86 (2H, m). m/z (ESI, +ve) 353.9 (M+H)+.

Provenance & Evidence