Potassium Carbonate → HCID 24946490, compound

Participants

Reaction Conditions

Reaction Steps

To a reaction vial (40 mL), is added 5-chloro-N-(4-(4-ethylpiperazin-1-yl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-8-amine (110 mg, 0.3 mmol), potassium carbonate (207 mg, 1.5 mmol, 5 eq.), 2-methoxypyridin-4-ylboronic acid (70 mg, 0.45 mmol, 1.5 eq), PddppfCl2 (44 mg, 20%), dioxane (4.0 mL) and water (1.0 mL). The reaction mixture is degassed and filled with argon. The reaction is heated at 105-110° C. for 20 h. After cooling to rt, ethyl acetate (10 mL) is added to each reaction vial. The organic phase is filtered through a pat of celite and then is evaporated to give a residue that is purified by silica gel column chromatography (1-3% 2N NH3 in MeOH/DCM) to give the title compound as a light yellow solid (90 mg, yield, 69.8%). 1H NMR (300 MHz, DMSO-d6): δ 8.75 (s, 1H), 8.56 (s, 1H), 8.26 (d, J=6.0 Hz, 1H), 7.60 (d, J=4.8 Hz), 7.58 (s, 1H), 7.46 (d, J=8.4 Hz, 1H), 7.25 (d, J=9.0 Hz, 2H), 6.96 (d, J=9.0 Hz, 2H), 6.93 (d, J=8.4 Hz, 1H), 3.91 (s, 3H), 3.12 (m, 4H), 2.50 (m, 4H), 2.36 (q, J=6.9, 2H), 1.04 (t, J=6.9 Hz, 3H); LCMS-ESI (m/z): calcd for C24H27N7O, 429; [M+H]+ found, 430.

Provenance & Evidence