Potassium Carbonate → N-(tert-butyl)-2-methoxy-5-(5-phenyl-4-(5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)pyrrolo[2,1-f][1,2,4]triazin-2-yl)pyridine-3-sulfonamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-chloro-5-phenyl-4-(5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)pyrrolo[2,1-f][1,2,4]triazine (30.0 mg, 0.0860 mmol) and N-(tert-butyl)-2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-sulfonamide (48.0 mg, 0.129 mmol) in 1,4-dioxane (3 mL) and water (0.5 mL) was added K2CO3 (24.0 mg, 0.173 mmol). The reaction mixture was purged with nitrogen gas for 10 min. PdCl2(dppf)-CH2Cl2 (7.04 mg, 8.63 μmol) was added and the reaction mixture heated at 100° C. for 12 h. The reaction mixture was allowed to cool to ambient temperature then filtered through CELITE® bed and the bed was washed with EtOAc (2×20 mL). The filtrate was diluted with water (20 mL) and extracted with EtOAc (3×15 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The resulting residue was purified by preparative HPLC (Condition B-97 as described in general methods) to obtain N-(tert-butyl)-2-methoxy-5-(5-phenyl-4-(5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)pyrrolo[2,1-f][1,2,4]triazin-2-yl)pyridine-3-sulfonamide (17.0 mg, 35.5%) as a pale yellow solid. LCMS Condition B-83: retention time 1.91 min, [M+1]=556.0. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.19 (s, 9H), 3.74 (s, 3H), 3.74 (br s, 2H), 3.74 (br s, 2H), 6.83 (d, J=2.7 Hz, 1H), 6.90 (s, 1H), 7.25 (dd, J=7.7 Hz, J=4.9 Hz, 1 H), 7.43-7.54 (m, 5H), 7.51 (d, J=1.7 Hz, 1H), 8.00 (d, J=2.7 Hz, 1H), 8.37 (d, J=3.6 Hz, 1H), 8.82 (d, J=2.6 Hz, 1H), 8.96 (d, J=2.6 Hz, 1H).

Provenance & Evidence