Ethyl Bromide → HCID 117925976, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 8-(pyridin-2-yl)pyrido[2,3-d]pyridazin-5(6H)-one 8 (50 mg, 0.22 mmol), ethyl bromide (20 μL, 0.27 mmol), potassium carbonate (303 mg, 2.2 mmol), and dimethylformamide (1.5 mL) was heated in a sealed tube at 60° C. for 30 minutes. After cooling to ambient temperature, the reaction mixture was poured into 15 mL of saturated brine and extracted with 3×20 mL of ethyl acetate. The combined organic extracts were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by normal phase flash chromatography eluting with 0-10% methanol in dichloromethane over 16 minutes Like fractions containing product were pooled, concentrated under reduced pressure, and dried at 60° C. overnight to give 6-ethyl-8-(pyridin-2-yl)pyrido[2,3-d]pyridazin-5(6H)-one (46 mg, 0.19 mmol), RL-6. 1H NMR (400 MHz, Chloroform-d) δ 9.15 (s, 1H), 9.02 (s, 1H), 8.80 (d, J=8.3 Hz, 1H), 8.23 (s, 1H), 8.04 (s, 1H), 7.71 (dd, J=8.1, 4.6 Hz, 1H), 7.56 (s, 1H), 4.48 (q, J=7.1 Hz, 2H), 1.52 (t, J=7.2 Hz, 3H). LCMS: (M+H)+, 253.

Provenance & Evidence