Sodium hydride → HCID 69675865, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N′-hydroxyacetimidamide (0.081 g, 1.093 mmol) and molecular sieves 4 Å (powder, 0.3 g) in THF (3.64 mL) was added 60% sodium hydride in mineral oil (0.109 g, 2.73 mmol) at rt and the mixture was stirred at 50° C. After being stirred at 50° C. for 30 min, a solution of methyl 2-(1-(tert-butoxycarbonylamino)ethyl)-6-fluoro-3-(pyridin-2-yl)quinoline-4-carboxylate (0.233 g, 0.547 mmol) in THF (1.822 mL) was added. The mixture was heated under reflux. After 3 h, the mixture was removed by filtration though a Celite™ pad and the pad was washed with DCM (2×100 mL). The organic filtrate was washed with water (100 mL), dried over Na2SO4, filtered, and concentrated in vacuo to give tert-butyl 1-(6-fluoro-4-(3-methyl-1,2,4-oxadiazol-5-yl)-3-(pyridin-2-yl)quinolin-2-yl)ethylcarbamate as a light yellow syrup: 1H NMR (400 MHz, DMSO-d6) δ ppm 8.60 (1H, d, J=4.5 Hz), 8.28 (1H, dd, J=9.3, 5.6 Hz), 7.83-7.94 (2H, m), 7.76 (1H, dd, J=10.0, 2.7 Hz), 7.38-7.51 (2H, m), 7.18 (1H, d, J=7.2 Hz), 4.89 (1H, quin, J=6.7 Hz), 2.38 (3H, s), 1.21-1.35 (12H, m); LC-MS (ESI) m/z 450.1 [M+H]+. The light yellow syrup was carried on crude without purification for the next step.

Provenance & Evidence