Phenyl ethenesulfonate → 1-Methyl-4-(vinylsulfonyl)piperazine

Participants

Reaction Conditions

Reaction Steps

7H-Indolo[2,1-a][2]benzazepine-10-carboxylic acid, 13-cyclohexyl-3-methoxy-6-(phenoxysulfonyl)-,1,1-dimethylethyl ester. To a solution of tbutyl 3-cyclohexyl-2-(2-formyl-4-methoxyphenyl)-1H-indole-6-carboxylate (4.40 g, 11.2 mmol) in dioxane (30.0 mL) and BEMP (4.88 mL, 16.9 mmol) was added phenyl vinylsulfonate (4.14 g, 22.5 mmol). The resulting mixture was stirred at 22° C. for 1 hr and then at 110° C. in a sealed tube in a microwave for 15 min. The resulting mixture was concentrated under reduced pressure. Silica gel chromatography (1:1 EtOAc:hexanes) of the concentrate afforded the title compound (3.49 g, 52%) as a yellow oil. MS m/z 600 (MH+), ret time 3.11 min, column B, 4 minute gradient, flow rate 4 mL/min.

Provenance & Evidence