A microwave vial containing a mixture of 4-((5-bromopyridin-2-yl)methyl)morpholine (537 mg, 2.09 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (583 mg, 2.30 mmol), KOAc (410 mg, 4.18 mmol) and PdCl2(dppf)-CH2Cl2 adduct (85 mg, 0.10 mmol) was flushed with nitrogen, dioxane (5 mL) was added. and the vial was sealed and heated at 100° C. for 6 hr. The reaction was filtered and the solid was washed with EtOAc. The filtrate was and washed with water, brine, and dried over MgSO4. Removal of the solvent left 750 mg of crude 4-((5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)methyl)morpholine (750 mg) as a brown thick oil that was used as such. A microwave vial containing a mixture of 2-bromo-7-morpholino-5H-pyrido[3,2-b]indole-4-carboxamide (60 mg, 0.14 mmol), 4-((5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)methyl)morpholine (130 mg, 0.171 mmol), PdCl2(dppf)-CH2Cl2 adduct (12 mg, 0.014 mmol) was flushed with nitrogen. DME (2.5 mL) and Na2CO3 (0.36 mL, 0.72 mmol, 2.0 M aq. solution) were added and the vial was sealed and heated at 100° C. for 5 hr. Preparative HPLC (100×30 mm Luna C18 column, Solvent A=10% Methanol, 90% H2O, 0.1% TFA; Solvent B=90% Methanol, 10% H2O, 0.1% TFA; gradient of 0 to 60% B over 10 min at 42 mL/min) followed by SCX capture and release with 2 N NH3 in MeOH gave 7-morpholino-2-(6-(morpholinomethyl)pyridin-3-yl)-5H-pyrido[3,2-b]indole-4-carboxamide (25 mg, 0.050 mmol, 35% yield) as a solid. MS (ESI) m/z 473.21 (M+H). 1H NMR (500 MHz, Acetone) δ ppm 10.75 (1H, s), 9.36 (1H, d, J=2.14 Hz), 8.58 (1H, dd, J=8.09, 2.29 Hz), 8.35 (1H, s), 8.10-8.22 (2H, m), 7.62 (1H, d, J=7.93 Hz), 7.29 (1H, d, J=2.14 Hz), 7.18 (1H, br. s.), 7.07 (1H, dd, J=8.85, 2.14 Hz), 3.80-3.87 (4H, m), 3.71 (2H, s), 3.64-3.69 (4H, m), 3.28-3.35 (4H, m), 2.47-2.57 (4H, m).
