Potassium Carbonate → N-(tert-Butyl)-2-isopropoxy-5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)pyrrolo[2,1-f][1,2,4]triazin-2-yl)pyridine-3-sulfonamide

Participants

Reaction Conditions

Reaction Steps

A solution of 2-chloro-5-phenyl-N-(pyridin-2-ylmethyl)pyrrolo[2,1-f][1,2,4]triazin-4-amine (50.0 mg, 0.149 mmol), N-(tert-butyl)-2-isopropoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-sulfonamide (89.0 mg, 0.223 mmol), K2CO3 (62.0 mg, 0.447 mmol) in 1,4-dioxane (20 mL) and water (6 mL) was purged with nitrogen gas for 10 min. PdCl2(dppf)-CH2Cl2 (6.08 mg, 7.45 mol) was added and the reaction mixture purged with nitrogen gas for further 5 min then heated to 100° C. for 12 h. The cooled reaction mixture was filtered through the CELITE® and washed with ethyl acetate (20 mL). The filtrate was washed with brine solution (10 mL). The organic layer was dried over sodium sulfate, filtered and evaporated under reduced pressure to give a residue that was purified by preparative HPLC (Condition B-91 as described in general methods) to give N-(tert-butyl)-2-isopropoxy-5-(5-phenyl-4-((pyridin-2-ylmethyl)amino) pyrrolo[2,1-f][1,2,4]triazin-2-yl)pyridine-3-sulfonamide (13.0 mg, 15.1%) as a pale yellow solid. LCMS Condition B-79: retention time 2.39 min, [M+1]=572.2. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.15 (s, 9H), 1.41 (d, J=6.5 Hz, 6H), 4.88 (d, J=5.0 Hz, 2H), 5.13 (quintet, J=6.7 Hz, 1H), 6.78 (d, J=2.5 Hz, 1H), 6.89 (s, 1H), 7.28 (t, J=5.5 Hz, 2H), 7.42-7.49 (m, 2H), 7.50-7.62 (m, 4H), 7.74-7.81 (m, 1H), 7.92 (d, J=2.5 Hz, 1H), 8.40-8.45 (m, 1H), 8.66 (d, J=2.5 Hz, 1H), 8.75 (d, J=2.5 Hz, 1H).

Provenance & Evidence