Potassium Carbonate → N-(tert-butyl)-5-(4-(((2-methylthiazol-4-yl)methyl)amino)-5-phenylpyrrolo[2,1-f][1,2,4]triazin-2-yl)pyridine-3-sulfonamide

Participants

Reaction Conditions

Reaction Steps

2-Chloro-N-((2-methylthiazol-4-yl)methyl)-5-phenylpyrrolo[2,1-f][1,2,4]triazin-4-amine (0.300 g, 0.843 mmol) and N-(tert-butyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-sulfonamide (0.574 g, 1.69 mmol) were dissolved in dioxane (25 mL) and water (3 mL). To the reaction mixture was added K2CO3 (0.350 g, 2.53 mmol) and the reaction mixture was degassed with nitrogen for 15 minutes. PdCl2(dppf)-CH2Cl2 (69.0 mg, 0.0840 mmol) was added and the resulting reaction mixture degassed with nitrogen for 20 minutes then heated to reflux at 110° C. for 14 h. The reaction mixture was allowed to cool and concentrated under reduced pressure. The residue was diluted with CH2Cl2 (2×25 mL) and filtered through CELITE®. The filtrate was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography using CombiFlash (REDISEP®, silica gel, 40 g, 25% EtOAc/hexanes) to afford N-(tert-butyl)-5-(4-(((2-methylthiazol-4-yl)methyl)amino)-5-phenylpyrrolo[2,1-f][1,2,4]triazin-2-yl)pyridine-3-sulfonamide (0.150 g, 28.0%). LCMS Condition B-82: retention time 2.35 min, [M+1]=534.2. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.15 (s, 9H), 2.62 (m, 3H), 4.88 (d, J=4.8 Hz, 2H), 6.75 (t, J=5.2 Hz, 1H), 6.85 (d, J=2.8 Hz, 1H), 7.36 (s, 1H), 7.42-7.57 (m, 5H), 7.94-7.97 (m, 2H) 8.91 (dd, J=2.0 Hz, J=2.4 Hz, 1H), 9.06 (d, J=2.4 Hz, 1H), 9.57 (d, J=2.0 Hz, 1H).

Provenance & Evidence