Sodium Carbonate → 6-Cyclopropyl-7-(5-fluoropyridin-3-yl)-1-methyl-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinoline

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 7-bromo-6-cyclopropyl-1-methyl-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinoline (147-8; 0.250 g, 0.00082 mol) and (5-fluoropyridin-3-yl)boronic acid (0.126 g, 0.009 mol) in the mixture of 1,4-dioxane (10 mL) and water (10 mL) was added sodium carbonate (0.260 g, 0.00246 mol). Reaction mass was purged with argon for 20 min. Then catalyst Pd(dppf)2Cl2 (0.066 g, 0.000082 mol) was added and allowed to stir at 80° C. for 12 h. The reaction mixture was filtered through CELITE bed and filter bed was thoroughly washed with ethyl acetate. The collected organic layer was concentrated under vacuum to afford the crude compound, which was purified by silica gel column chromatography to obtain title compound. 1H NMR (400 MHz, DMSO-d6) δ 8.587-8.580 (d, J=2.8 Hz, 1H), 8.548 (s, 1H), 7.881-7.856 (d, J=10 Hz, 1H), 7.679-7.658 (d, J=8.4 Hz, 1H), 7.401-7.380 (d, J 8.4 Hz, 1H), 3.237-3.203 (t, J=6.8 Hz, 2H), 3.050-3.016 (t, J=7.2 Hz, 2H), 2.671 (s, 3H), 2.175 (s, 1H), 0.759-0739 (d, J 8 Hz, 2H), 0.034-0.022 (d, J=4.8 Hz, 2H), MS (M+1): 321.2.

Provenance & Evidence