Sodium Hydroxide → 1-(7-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridine-6-carboxamide

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Reaction Steps

1-(7-Fluoro-3-methyl-2-(pyridin-2-yl)quinolin-4-yl)-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridine-6-carbonitrile (80 mg, 0.195 mmol) in EtOH (3 mL) was treated with sodium hydroxide (156 mg, 3.91 mmol) in water (1.0 mL). The reaction was heated at reflux for 3 h. After this time the reaction was evaporated in vacuo. Reverse phase HPLC (10% to 60% acetonitrile in water) gave 1-(7-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridine-6-carboxamide. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.72 (1H, ddd, J=4.8, 1.8, 1.1 Hz), 8.34 (1H, d, J=1.8 Hz), 7.99-8.06 (1H, m), 7.80-7.96 (4H, m), 7.48-7.61 (2H, m), 7.31 (1H, br. s.), 6.61 (1H, d, J=1.8 Hz), 3.90-3.99 (1H, m), 3.85 (1H, d, J=9.4 Hz), 2.27 (3H, s), 1.53 (3H, s), 1.45 (3H, s). Mass Spectrum (ESI) m/e=428 (M+1).

Provenance & Evidence