Triethylamine → HCID 53252015, compound

Participants

Reaction Steps

A solution of 3-bromo-7,8,9,10-tetrahydrocyclohepta[d]pyrido[1,2-a]pyrimidin-11(6H)-one (250 mg, 0.85 mmol), 1-ethynyl-4-fluorobenzene (255 mg, 2.12 mmol), Pd(OAc)2 (38.2 mg, 0.17 mmol), PPh3 (200 mg, 0.76 mmol), CuI (16.2 mg, 0.085 mmol), and Et3N (0.7 mL) in DMF (8 mL) was stirred in a sealed tube at 70° C. for 3.5 hours. After it was cooled to room temperature, the reaction mixture was diluted with H2O and extracted with ethyl acetate (2×50 mL). The combined organic layers were washed with brine and dried over anhydrous sodium sulfate. After filtration and concentration, the crude product was purified by silica gel to produce 185 mg of desired product. MS (ESI): 333 (MH+); 1H NMR (300 MHz, CDCl3) δ 8.97-8.94 (dd, J=7.44, 0.66 Hz, 1H), 7.65-7.56 (m, 3H), 7.15-7.06 (m, 3H), 3.00-2.97 (m, 4H), 1.94-1.88 (m, 2H), 1.80-1.64 (m, 4H). mGluR5 PAM EC50: +++++. Fold shift at 10 μM: +.

Provenance & Evidence