Styrene → HCID 58574509, compound

Participants

Reaction Steps

A solution of 6-bromo-2-methyl-2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-one (100 mg, 0.36 mmol), styrene (75 mg, 0.72 mmol), Pd (PPh3)4 (45 mg, 0.036 mmol), PPh3 (1 mg, 0.0036 mmol) and Et3N (182 mg, 1.8 mmol) in DMF (10 mL) was stirred at 140° C. under N2 for 8 hours. After cooled to room temperature, the mixture was diluted with H2O and extracted with EtOAc. The combined organic layer was washed with brine and dried over Na2SO4. Then the filtrate was concentrated and purified by column chromatography to give the desired product (67 mg). MS (ESI): 303 (MH+); 1H NMR (300 MHz, DMSO-d6) δ 8.13-8.10 (d, J=8.3 Hz, 1H), 7.87-7.84 (d, J=8.4 Hz, 1H), 7.80 (s, 1H), 7.70-7.68 (d, J=7.5 Hz, 2H), 7.56-7.47 (m, 2H), 7.44-7.40 (m, 2H), 7.35-7.30 (m, 1H), 4.29-4.22 (dd, J=11.7, 7.8 Hz, 1H), 3.68-3.62 (dd, J=11.7, 6.8 Hz, 1H), 3.38-3.29 (dd, J=17.2, 8.1 Hz, 1H), 2.91-2.83 (dd, J=17.2, 7.5 Hz, 1H), 2.75-2.67 (m, 1H), 1.18-1.16 (d, J=6.7 Hz, 3H). mGluR5 PAM EC50: +++.

Provenance & Evidence