Dichloromethane → HCID 57524677, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of tert-butyl 2-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)-9-methyl-5-oxo-5,7,8,9-tetrahydro-6H-pyrido[3′,4′:4,5]pyrrolo[2,3-b]pyridine-6-carboxylate (crude, ca. 0.37 mmol) in CH2Cl2 (4 mL) at 0° C. was added TFA (0.4 mL). The resulting solution was stirred at 0° C. for 1 h, quenched with saturated NaHCO3 solution (10 mL), and extracted with CH2Cl2 (3×10 mL). The combined organic extractions were dried over Na2SO4 and concentrated under reduced pressure to dryness. Preparative thin layer chromatography (200:10:1 CH2Cl2/MeOH/NH4OH) provided the title compound (49 mg, 33% over 2 steps) as an off-white solid: 1H NMR (300 MHz, DMSO-d6) δ 8.28 (d, J=8.2 Hz, 1H), 7.84 (d, J=7.7 Hz, 1H), 7.49-7.34 (m, 6H), 7.25 (br t, 1H), 6.18 (dd, J=7.8, 2.7 Hz, 1H), 6.01 (d, J=2.7 Hz, 1H), 5.17 (s, 2H), 3.76 (s, 3H), 3.53 (td, J=6.9, 2.4 Hz, 2H), 3.09 (t, J=6.9 Hz, 2H); ESI MS m/z 401 [M+H]+; HPLC (Method B) 99.0% (AUC), tR=14.6 min.

Provenance & Evidence