4-Chloroquinoline → 5-(Quinolin-4-yl)-3-(1-Methylpiperidin-4-yl)-4-Aza-1H-Indole

Participants

Reaction Conditions

Reaction Steps

O-Trifluoromethanesulfonyl-3-(1-methylpiperidin-4-yl)-5-hydroxy-4-aza-1H-indole (239 mg, 0.658 mmol), tetrakis(triphenylphosphine)palladium(0) (76 mg, 0.065 mmol), dried lithium chloride (167 mg, 3.95 mmol), 4-chloroquinoline (108 mg, 0.658 mmol), hexamethylditin (215 mg, 0.658 mmol), and 15 mL of 1,4-dioxane were placed in a flask and heated to reflux (about 105° C.). The reaction was stirred for about 18 hours before 50 mL of 8M aqueous potassium fluoride solution was added. The solution was extracted with 3:1 chloroform:isopropanol and brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel flash chromatography (0-10% methanol:dichloromethane) to give 103 mg of the title compound. (46%). MS(FD) m/e 343.2 (M+H). EA calculated for C22H22N4: C, 77.16; H, 6.48; N, 16.36. Found: C, 76.98; H, 6.55; N, 16.29.

Provenance & Evidence