Triethylamine → N-(1-benzyl-2,3-dihydro-1H-indole-5-yl)-methanesulfonamide

Participants

Reaction Conditions

Reaction Steps

1-benzyl-5-nitro-2,3-dihydro-1H-indole (100 mg, 0.39 mmol) was dissolved in tetrahydrofuran (1 ml) and methanol (1 ml), and ammonium formate (124mg, 1.96 mmol, 5 equivalent) and palladium carbon (10%) of a catalytic amount were added. Then, the solution was stirred at 40° C. for 10 minutes to complete the reduction. After completing the reaction, the solution was filtered through celite, concentrated under reduced pressure, dissolved again in ethyl acetate (10 ml), washed with water and salt solution, dried over anhydrous magnesium sulfate, concentrated again under reduced pressure and then, dried completely under a high-degree vacuum. Afterward, the obtained residue was dissolved with dichloromethane (2.0 ml), cooled to 0° C., blended with triethylamine (0.055 ml, 0.39 mmol) and mesyl chloride (0.031 ml, 0.40 mmol) and then, stirred at the same temperature for 30 minutes to complete the reaction. After pouring water (2.0 ml) again at room temperature, dichloromethane layer was separated, washed with brine, dried over anhydrous magnesium sulfate, and concentrated. Finally, the residue was purified through flash column chromatography (an eluent:ethyl acetate/n-hexane=1/2, v/v). As a result, the present compound (90 mg, productive yield 76%) was obtained.

Provenance & Evidence