Aluminium lithium hydride → HCID 59631308, compound

Participants

Reaction Conditions

Reaction Steps

The 1-(3-(5,7-difluoro-3-methyl-4-(5-morpholinopyridin-3-ylamino)quinolin-2-yl)-4-(methylsulfonyl)phenyl)ethanone (40 mg, 0.072 mmol) was dissolved in THF (1.00 mL) and cooled to 0° C. To the solution was added 1M lithium aluminum hydride (0.072 mL, 0.072 mmol) in THF and the reaction mixture was allowed to warm to rt over a period of 1.5 h. The reaction was then worked up via the method found in the Fieser and Fieser (Vol. 1) and the mixture was filtered over a short plug of silica gel and washed with EtOAc. The filtrate was cond to give (+/−)-1-(3-(5,7-difluoro-3-methyl-4-(5-morpholinopyridin-3-ylamino)-quinolin-2-yl)-4-(methylsulfonyl)-phenyl)ethanol. 1H NMR (CDCl3) δ ppm 8.14 (1H, dd, J=8.2, 4.1 Hz), 7.93 (1H, t, J=2.4 Hz), 7.75 (1H, dd, J=4.1, 2.5 Hz), 7.68 (1H, ddd, J=18.5, 8.3, 1.6 Hz), 7.42-7.58 (3H, m), 7.09 (1H, ddd, J=13.4, 8.6, 2.5 Hz), 6.63-6.73 (1H, m), 5.06 (1H, q, J=6.7 Hz), 3.78 (4H, t, J=4.8 Hz), 3.20 (4H, q, J=3.9 Hz), 3.12 (3H, d, J=1.6 Hz), 1.91 (3H, d, J=5.3 Hz), 1.57 (3H, d, J=6.7 Hz). Mass Spectrum (ESI) m/e=555.2 (M+1).

Provenance & Evidence