Ethyl Acetate → HCID 86608823, compound

Participants

Reaction Steps

N-{(1R)-1-[2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethyl}-1-[(trifluoroacetyl)amino]cyclopropanecarboxamide (250 mg, 0.563 mmol), 8-bromoquinoline (117 mg, 0.563 mmol), cesium carbonate (367 mg, 1.13 mmol), and bis(tri-t-butylphosphine) palladium(0) (10 mg, 0.03 mmol) were stirred in 1 mL of anhydrous dioxane overnight at 90° C. in a sealed tube. The reaction mixture was cooled to room temperature and diluted w/EtOAc. The organic layer was separated, washed with water and brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude material was purified by silica gel chromatography eluting with 10% to 95% EtOAc/hexanes to provide (N-[(1R)-1-(2-fluoro-4-quinolin-8-ylphenyl)ethyl]-1-[(trifluoroacetyl)amino]cyclopropanecarboxamide. ES MS, M+H+ found: 475. Proton NMR (400 MHz, CDCl3) δ 1.2 (m, J=2.4 Hz, 2H), 1.58 (d, J=6.8 Hz, 3H), 1.7 (m, J=2.9 Hz, 2H), 3.86 (s, 3H), 5.33 (q, J=7.2 Hz, 1H), 6.64 (d, J=8.8 Hz, 1H), 6.84 (s, 1H), 7.08 to 7.19 (m, 3H), 7.34 (m, 3H), 7.47 (m, J=4.5 Hz, 1H), 7.81 (m, J=5 Hz, 1H), 7.9 (d, J=9 Hz, 1H).

Provenance & Evidence