[Cl:1][C:2]1[CH:3]=[C:4](B2OC(C)(C)C(C)(C)O2)[CH:5]=[C:6]2[C:11]=1[N:10]1[C:12]([CH3:15])=[N:13][N:14]=[C:9]1[CH2:8][CH2:7]2.Br[C:26]1[CH:27]=[N:28][CH:29]=[C:30]([F:34])[C:31]=1[CH2:32][CH3:33].C(=O)([O-])[O-].[Na+].[Na+].ClCCl>O.O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:26]2[CH:27]=[N:28][CH:29]=[C:30]([F:34])[C:31]=2[CH2:32][CH3:33])[CH:5]=[C:6]2[C:11]=1[N:10]1[C:12]([CH3:15])=[N:13][N:14]=[C:9]1[CH2:8][CH2:7]2To a stirred solution of 9-chloro-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 (80-4; 0.717 g, 0.0020 mol) and 3-bromo-4-ethyl-5-fluoropyridine (0.423 g, 0.0020 mol) in the mixture of 1,4-dioxan (5 mL) and water (5 mL) was added sodium carbonate (0.66 g, 0.0062 mol). Reaction mass was purged with argon for the next 20 min. Catalyst Pd(dppf)2Cl2.dichloromethane (0.084 g, 0.0001 mol) was added and again purged with argon for 10 min and allowed to stirred at 90° C. for 4 h. The reaction mixture was filtered through CELITE bed and filter bed was thoroughly washed with ethyl acetate. The collected organic parts was concentrated under vacuum to afford the crude compound, which was purified by silica gel column chromatography followed by preparative HPLC (analytical conditions; column: ZORBAX XDB (150 mm×4.6 mm×3.5 μm), mobile phase (A): water, Mobile phase (B): MeOH, flow rate: 1.0 mL/min, gradient T/% B:0/20,6/25,25/75,27/20,30/20) to obtain title compound. 1H NMR (400 MHz, DMSO-d6) δ: 8.55 (s, 1H), 8.32 (s, 1H), 7.64 (s, 1H), 7.55 (s, 1H), 2.94 (bs, 4H), 2.65-2.59 (m, 2H), 2.56 (s, 3H), 1.09-1.05 (t, J=7.6 Hz, 3H). MS (M+1): 343.2.
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