Sodium hydride → HCID 58561015, compound

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (60 wt % in mineral oil, 15.5 mg, 0.387 mmol) was washed with hexanes (2 mL), then a solution of 6-chloro-8-methylquinolin-4-ol (50.0 mg, 0.258 mmol) in DMF (2 mL) was added. Once gas evolution had ceased, the product of Step A (170 mg, 0.387 mmol) was added in one portion, then the mixture was stirred at 120° C. overnight. After being allowed to cool to room temperature, the mixture was diluted with EtOAc (20 mL) and water (15 mL), then the organic layer was concentrated. The resulting residue was purified by silica gel chromatography eluting with 0-100% EtOAc/hexanes to afford the title compound. 1H NMR (500 MHz, CDCl3): δ 8.51 (d, J=5 Hz, 1H); 7.93 (d, J=8.5 Hz, 2H); 7.89 (d, J=2.5 Hz, 1H); 7.47 (s, 1H); 7.26 (dd, J=6.5, 6.0 Hz, 4H); 7.12 (d, J=8.5 Hz, 2H); 6.43 (d, J=5 Hz, 1H); 5.44 (d, J=6.5 Hz, 1H); 3.29-3.23 (m, 1H); 2.69 (s, 3H); 1.90-1.80 (m, 1H); 1.74-1.64 (m, 1H); 1.58 (s, 9H); 1.30-1.10 (m, 2H); 0.83 (t, J=7.5 Hz, 3H); LC4 2.78 min. (M+H)+ 550.

Provenance & Evidence