Triethylamine → HCID 58574283, compound

Participants

Reaction Steps

A solution of 7,7-dimethyl-3-vinyl-8,9-dihydro-6H-pyrido[2,1-b]quinazolin-11(7H)-one (116 mg, 0.4 mmol, 1 equiv), 1-bromo-2-fluorobenzene (140 mg, 0.8 mmol, 2 equiv), Cs2CO3 (260 mg, 0.8 mmol, 2 equiv), Pd(OAc)2 (576 mg, 0.08 mmol, 0.2 equiv), Ph3P (88 mg, 0.32 mmol, 0.8 equiv), Et3N (80 mg, 0.8 mmol, 2 equiv) and (n-Bu)4NI (256 mg, 0.8 mmol, 2 equiv) in NMP was stirred at 140° C. for 20 minutes in a microwave reactor. After that, the reaction mixture was cooled to rt. The reaction was quenched with water (20 mL) and extracted with ethyl acetate (3×20 mL). The organic combined organic layers were dried over Na2SO4 and concentrated. The crude was purified by silica gel chromatography to produce 53 mg desired product. MS (ESI): 349 (MH+); 1H NMR (300 MHz, CD3OD) δ 8.20-8.17 (d, J=8.12 Hz, 1H), 7.80-7.68 (m, 2H), 7.56 (s, 1H), 7.43-7.19 (m, 3H), 7.15-6.99 (m, 2H), 4.12-3.92 (t, J=13.20 Hz, 2H), 2.82 (s, 2H), 1.85-1.72 (t, J=12.84 Hz, 2H), 1.15 (s, 6H). mGluR5 PAM EC50: +++.

Provenance & Evidence