Ethyl 3-(4-fluorobenzoyl)-1,2,3,6-tetrahydroazepino[4,5-b]indole-5-carboxylate → HCID 11463248, compound

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Reaction Steps

A solution of 3-(4-fluoro-benzoyl)-1,2,3,6-tetrahydro-azepino[4,5-b]indole-5-carboxylic acid ethyl ester (Example 5, 1.3 g, 3.4 mmol) in 60 mL of glacial acetic acid containing 500 mg of Adams catalyst was subjected to hydrogenation for 14 hours at room temperature and under 45psi of hydrogen. (Boekelheide, V. and Liu, C-T, J. Am. Chem. Soc. 1952, 74, 4920-4922). The catalyst was removed by filtration and the filtrate was concentrated in vacuo. The crude product was purified by preparative normal-phase HPLC eluting with 40% EtOAc-Hexane . 1H-NMR(CDCl3): δ 7.99 (1H, s), 7.40-7.37 (2H, m), 7.11-7.06 (2H, m), 4.22-4.15 (4H, m), 3.54 (1H, m), 2.75 (1H, m), 2.54-2.45 (2H, m), 2.31 (2H, m), 1.76 (4H, m), 1.61 (2H, m), 1.32 (3H, m); MS (ES): 385 (MH+).

Provenance & Evidence