Hexamethylphosphoramide → 1-(2,3-Dichlorobenzoyl)-5-methoxy-2-methyl-(3-(morpholin-4-yl)ethyl)-1H-indole hydrochloride

Participants

Reaction Conditions

Reaction Steps

To 5-methoxy-2-methyl-3-(2-(morpholin-4-yl)ethyl)- 1H-indole (311 mg; 1.13 mmol) in 10 mL dry THF at -78° C. was added HMPA (590 μL; 3.39 mmol), then dropwise KHMDS (0.5M in Tol; 2.5 mL; 1.25 mmol). The solution was stirred 30 min at -22° C. then cooled to -78° C. after which 2,3-dichlorobenzoyl chloride (361 mg; 1.72 mmol) was added. The final mixture was allowed to reach r.t. slowly then stirred 1 h. The mixture was poored in saturated NaHCO3 (25 mL), extracted with EtOAc (2×50 mL). The organic phase was washed with brine (50 mL), dried over Na2SO4, filtered, concentrated and flash chromatographed (Silica gel; EtOAc) to yield 503 mg (99%) of the title compound.

Provenance & Evidence