Styrene → HCID 53250274, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-bromo-7,8,9,10-tetrahydroazepino[2,1-b]quinazolin-12(6H)-one (100 mg, 0.34 mmol), Cs2CO3 (132.6 mg, 0.85 mmol), Pd(OAc)2 (30.6 mg, 0.14 mmol), PPh3 (103 mg, 0.34 mmol), Bu4NBr (109.5 mg, 0.34 mmol), and styrene (88.7 mg, 0.85 mmol) in DMF (6 mL) in a sealed tube was stirred at 120° C. for two hours. After it was cooled to room temperature, the reaction mixture was quenched with water (20 mL) and extracted with ethyl acetate (3×20 mL). The combined organic layers were dried over Na2SO4. After filtration and concentration, the residue was purified by silica gel chromatography to give the desired product. MS (ESI): 317 (MH+); 1H NMR (300 MHz, CDCl3) δ 8.08-8.05 (d, J=8.19 Hz, 1H), 7.78-7.74 (m, 2H), 7.68-7.66 (m, 2H), 7.54-7.30 (m, 5H), 4.34-4.31 (m, 2H), 3.05 (broad, 2H), 1.73-1.70 (m, 6H). mGluR5 PAM EC50: +++++. Fold shift at 10 μM: ++.

Provenance & Evidence