4-Acetamidobenzenesulfonyl azide → Benzyl 5-diazo-1-(3,4-dichlorobenzyl)-4-oxo-4,5,6,7-tetrahydroindole-2-carboxylate

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Reaction Steps

Triethyl amine (0.36 mL) was added dropwise to a solution of benzyl 1-(3,4-dichlorobenzyl)-5-formyl-4-oxo-4,5,6,7-tetrahydroindole-2-carboxylate (0.5 g) and p-acetamidobenzenesulphonyl azide (305 mg) at room temperature, and stirred for 18 hours to give a brown solution. The solvent was removed in vacuo to afford a brown oil. Purification by column chromatography, using iso-hexane : 20% ethyl acetate as eluent afforded the title compound as a pale yellow solid (0.31 g, 62%), NMR d(CDCl3) 2.80 (2H, t), 3.05 (2H, t), 5.13 (2H, s), 5.57 (2H, s), 6.76 (1H, dd), 7.05 (1H, s), 7.20-7.40 (7H, m); M/z (+) 456, 454 (M+).

Provenance & Evidence