tert-Butyl 9-methyl-2-(2-oxo-4-(6-(trifluoromethyl)pyridin-3-yl)pyridin-1(2H)-yl)-5,7,8,9-tetrahydro-6H-pyrido[3',4':4,5]pyrrolo[2,3-b]pyridine-6-carboxylate → 1-(9-Methyl-5,7,8,9-tetrahydro-6H-pyrido[3',4':4,5]pyrrolo[2,3-b]pyridin-2-yl)-4-(6-(trifluoromethyl)pyridin-3-yl)pyridin-2(1H)-one

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Reaction Steps

To a solution of tert-butyl 9-methyl-2-(2-oxo-4-(6-(trifluoromethyl)pyridin-3-yl)pyridin-1(2H)-yl)-5,7,8,9-tetrahydro-6H-pyrido[3′,4′:4,5]pyrrolo[2,3-b]pyridine-6-carboxylate (0.81 g, 1.6 mmol) in CH2Cl2 (8.0 mL) was added 1.25 M HCl in MeOH (30 mL), and the resulting suspension was stirred at ambient temperature for 18 h. The suspension was diluted with CH2Cl2 (18 mL), 1.25 M HCl in MeOH (6.0 mL) was added, and the resulting suspension was stirred at ambient temperature for 72 h. The suspension was diluted with Et2O (50 mL), and the resulting solids were collected by filtration, dissolved in CH2Cl2 (30 mL), and washed with saturated NaHCO3 solution (50 mL). The resulting layers were separated, and the organic layer was concentrated under reduced pressure to dryness. Flash chromatography (40 g ISCO column, CH2Cl2/(80:18:2 CH2Cl2/MeOH/NH4OH), 100:0 for 1 column volume, increased to 0:100 over 12 column volumes and held for 30 column volumes) provided the title compound (0.50 g, 75%) as a yellow powder: 1H NMR (500 MHz, DMSO-d6) δ 9.20 (d, J=2.0 Hz, 1H), 8.50 (dd, J=8.0, 2.0 Hz, 1H), 8.10-8.02 (m, 2H), 7.94 (d, J=8.0 Hz, 1H), 7.35 (d, J=8.5 Hz, 1H), 7.02 (d, J=2.0 Hz, 1H), 6.83 (dd, J=7.5, 20 Hz, 1H), 3.89 (s, 2H), 3.68 (s, 3H), 3.09 (t, J=5.5 Hz, 2H), 2.76 (t, J=5.5 Hz, 2H).

Provenance & Evidence