Hydrochloric Acid → 4-(Benzyloxy)-1-(9-methyl-5,7,8,9-tetrahydro-6H-pyrido[3',4':4,5]pyrrolo[2,3-b]pyridin-2-yl)pyridin-2(1H)-one

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Reaction Steps

tert-Butyl 2-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)-9-methyl-5,7,8,9-tetrahydro-6H-pyrido[3′,4′:4,5]pyrrolo[2,3-b]pyridine-6-carboxylate (0.51 g, 1.1 mmol) was treated with 1.25 M HCl in MeOH (25 mL), and the resulting solution was stirred at ambient temperature for 18 h. The solution was concentrated to dryness under reduced pressure. The resulting residue was diluted with CH2Cl2 (30 mL) and washed with saturated NaHCO3 solution (50 mL). The resulting layers were separated, and the aqueous phase was extracted with CH2Cl2 (3×30 mL). The combined organic extractions were dried over Na2SO4 and concentrated under reduced pressure to dryness. Flash chromatography (40 g ISCO column, CH2Cl2/(80:18:2 CH2Cl2/MeOH/NH4OH), 100:0 for 4 column volumes, increased to 0:100 over 4 column volumes and held for 10 column volumes) provided the title compound (0.24 g, 59%) as an off-white film: 1H NMR (300 MHz, DMSO-d6) δ 7.87 (d, J=8.1 Hz, 1H), 7.79 (d, J=7.8 Hz, 1H), 7.49-7.37 (m, 5H), 7.23 (d, J=8.1 Hz, 1H), 6.15 (dd, J=7.5, 2.7 Hz, 1H), 5.98 (d, J=2.7 Hz, 1H), 5.16 (s, 2H), 3.87 (s, 2H), 3.65 (s, 3H), 3.07 (t, J=5.1 Hz, 2H), 2.79-2.61 (m, 2H).

Provenance & Evidence