Dimethylformamide → HCID 58574762, compound

Participants

Reaction Steps

A solution of 3-bromo-8-methyl-7,8,9,10-tetrahydroazepino[2,1-b]quinazolin-12(6H)-one (100 mg, 0.42 mmol), styrene (100 mg, 0.33 mmol), Cs2CO3 (128 mg, 0.396 mmol), Bu4NBr (106 mg, 0.33 mmol), PPh3 (43.2 mg, 0.165 mmol) and Pd(OAc)2 (7.4 mg, 0.033 mmol) in DMF (10 mL) was stirred at 140° C. in a sealed tube for 8 hours. After it was cooled to room temperature, the mixture was diluted with H2O and extracted with EtOAc. The combined organic layers were washed with brine and dried over Na2SO4. Then the filtration was concentrated and purified by column chromatography to give the desired product. MS (ESI): 332 (MH+); 1H NMR (300 MHz, CD3OD) δ 8.84-8.83 (d, J=5.73 Hz, 1H), 8.68-8.62 (m, 1H), 8.53-8.51 (d, J=8.22 Hz, 1H), 8.43-8.41 (d, J=8.37 Hz, 1H), 8.20-8.10 (m, 2H), 8.06 (s, 1H), 8.03-7.98 (t, J=13.57 Hz, 1H), 7.74-7.69 (d, J=16.47 Hz, 1H), 5.24-5.17 (dd, J=14.92, 6.84 Hz, 1H), 3.95-3.86 (m, 1H), 3.51-3.37 (m, 2H), 2.24-2.01 (m, 3H), 1.64-1.52 (m, 1H), 1.45-1.33 (m, 1H), 1.07-1.05 (d, J=6.45 Hz, 3H). mGluR5 PAM EC50: ++.

Provenance & Evidence