4-Toluenesulfonyl chloride → 5-chloro-N-[1-(2-chloroethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-1H-indole-2-carboxamide

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Reaction Steps

p-Toluenesulphonyl chloride (285 mg, 1.49 mmol) was added to a solution of 5-chloro-N-[1-(2-hydroxyethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-1H-indole-2-carboxamide (Example 36; 286 mg, 0.75 mmol) in pyridine (2 mL) under an inert atmosphere and stirred at ambient temperature for 18 hours. The mixture was diluted with THF (10 mL) and EtOAc (50 mL) and washed with 1M HCl aq. (20 mL), water (20 mL), brine (20 mL), dried (MgSO4), filtered and evaporated. The residue was purified by column chromatography (DCM to DCM:THF (9:1)) to afford the title compound (144 mg, 40%) as a yellow solid.

Provenance & Evidence