Hydrochloric Acid → 1-(1-(2-Morpholinoethyl)-1H-indazol-5-yl)-4-(4-(trifluoromethyl)phenyl)pyridin-2(1H)-one

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Reaction Steps

To a solution of 2-(5-(2-oxo-4-(4-(trifluoromethyl)phenyl)pyridin-1(2H)-yl)-1H-indazol-1-yl)acetaldehyde (84 mg, 0.21 mmol) in CH2Cl2 (4.0 mL), MeOH (1.0 mL) and AcOH (0.50 mL) was added morpholine (0.06 mL, 0.7 mmol) and picoline-borane complex (25 mg, 0.23 mmol). After stirring at ambient temperature under nitrogen atmosphere for 1.5 h, the solution was treated with 1 N HCl (10.0 mL) and stirred vigorously for 30 minutes. The mixture was made basic with saturated aqueous NaHCO3 (25 mL) and extracted with CH2Cl2 (3×25 mL). The organics were dried over Na2SO4, filtered and concentrated to dryness. Purification by flash chromatography (silica gel, CH2Cl2/MeOH, 97:3) gave the title compound (33 mg, 33%) as an off-white solid: 1H NMR (500 MHz, CDCl3) δ 8.14 (d, J=0.7 Hz, 1H), 7.95 (d, J=8.1 Hz, 2H), 7.85-7.77 (m, 5H), 7.48 (dd, J=8.9, 1.9 Hz, 1H), 6.95 (d, J=1.8 Hz, 1H), 6.85 (dd, J=7.1, 2.0 Hz, 1H), 4.63 (t, J=6.5 Hz, 2H), 3.64-3.62 (m, 4H), 2.91 (t, J=6.5 Hz, 2H), 2.54-2.52 (m, 4H); ESI MS m/z 469 [M+H]+.

Provenance & Evidence