Sodium Carbonate → HCID 89961587, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 1-methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinoline (75-2; 0.5 g, 0.00112 mol) and 3-bromo-5-(trifluoromethyl)pyridine (0.381 g, 0.00168 mol) in the mixture of 1,4-dioxan (10 mL) was added aqueous sodium carbonate (2M) (1.68 mL, 0.003376 mol). Reaction mass was purged with argon for 20 min. Then catalyst Pd(dppf)2Cl2 (0.0459 g, 0.003376 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 parts were 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 9.25 (s, 1H), 8.97 (s, 1H), 8.51 (s, 1H), 8.02 (s, 1H), 7.91-7.89 (d, J 8.4 Hz, 1H), 7.78-7.76 (d, J=8 Hz, 1H), 3.04 (s, 4H), 2.70 (s, 3H). MS (M+1): 331.1.

Provenance & Evidence