7-Chloro-1H-pyrrolo[3,2-b]pyridine → {1-(4-chlorobenzyl)-2-oxo-2-[4-(1H-pyrrolo[3,2-b]pyridin-7-yl)-piperazin-1-yl]-ethyl}-carbamic acid tert-butyl ester

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Reaction Steps

To a solution of 7-Chloro-1H-pyrrolo[3,2-b]pyridine (40 mg, 0.262 mmol) in xylene (4 mL) and TEA (1 mL) was added [1-(4-chlorobenzyl)-2-oxo-2-piperazin-1-yl-ethyl]-carbamic acid tert-butyl ester (0.1 g, 0.27 mol). The mixture was refluxed for 6 days. The solvent was removed under vacuum and the residue was subject to purification by HPLC to afford {1-(4-chlorobenzyl)-2-oxo-2-[4-(1H-pyrrolo[3,2-b]pyridin-7-yl)-piperazin-1-yl]-ethyl}-carbamic acid tert-butyl ester (10 mg, 8%). 1H NMR (CDCl3, 400 Hz) δ 11.81 (s, 1H), 7.95 (d, J=6.4 Hz, 1H), 7.40 (s, 1H), 7.15 (d, J=8.00 Hz, 2H), 6.46 (d, J=6.8 Hz, 2H), 5.42 (d, J=8.4 Hz, 1H), 4.82 (d, J=7.2 Hz, 1H), 3.87-3.28 (m, 8H), 2.98 (d, J=6.4 Hz, 2H), 1.41 (s, 9H). MS (ESI+) [M+H]+ 484.

Provenance & Evidence