In a glass pressure tube was added 5-bromo-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-methyl-3-(1-methylethyl)-1H-indole-7-carboxamide (225 mg, 0.523 mmol), 4-(N,N-dimethylaminomethyl)phenylboronic acid pinacol ester hydrochloride (200 mg, 0.672 mmol), potassium phosphate (340 mg, 1.602 mmol), dioxane (12 mL) and water (3 mL). The reaction was stirred and purged with N2 then PdCl2 (dppf)-CH2Cl2 adduct (40 mg, 0.049 mmol) was added. The reaction was capped and stirred at 110° C. for 4 h LCMS indicated that the reaction was complete. The dark black reaction was transferred to a round bottom flask and evaporated to dryness. The crude material was purified by silica gel chromatography (Analogix, SF25-40 g, 0 to 70% CH2Cl2/20% (5% NH4OH in MeOH) in CH2Cl2). A short DASi column was used and the compound loaded as a suspension in CH2Cl2. The pure fractions were combined and evaporated to dryness to give the product as a very dark brown-black solid. The solid was taken up in CH2Cl2 and treated with Silicycle Si-Thiol derivatized silica gel (2 g, 1.46 mMol/g, cat. no. R51030B). After swirling for ˜30 minutes the mixture was filtered through a pad of Celite, washed with CH2Cl2, and evaporated to dryness. The now light yellow colored solid was dissolved in a small amount of CH2Cl2, triturated with hexanes, filtered and dried under vacuum to give 5-{4-[(dimethylamino)methyl]phenyl}-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-methyl-3-(1-methylethyl)-1H-indole-7-carboxamide (95 mg, 0.196 mmol, 37.5% yield) as a light tan solid. 1H NMR (400 MHz, DMSO-d6) δ 11.50 (s, 1H), 8.50 (t, J=4.93 Hz, 1H), 7.83 (d, J=1.52 Hz, 1H), 7.68 (s, 1H), 7.66 (s, 1H), 7.40 (s, 1H), 7.38 (s, 1H), 7.33 (d, J=1.52 Hz, 1H), 7.10 (s, 1H), 5.87 (s, 1H), 4.36 (d, J=5.05 Hz, 2H), 3.69 (s, 3H), 3.34 (br. s., 3H), 3.22 (dt, J=6.73, 13.58 Hz, 1H), 2.26 (br. s., 6H), 2.24 (s, 2H), 2.11 (s, 3H), 1.31 (d, J=6.82 Hz, 6H). MS (ES)+m/e 485.3 [M+H]+.
