Benzyl Bromide → 3-Benzyl-1,2,3,6-tetrahydroazepino[4,5-B]indole-5-carboxylic acid ethyl ester

Sodium hydride (60% in mineral oil, 320 mg, 8 mmol) was added to a stirred solution of ethyl 1,2,3,6-tetrahydroazepino[4,5-b]indole-5-carboxylate (520 mg, 2 mmol) in anhydrous DMF (8 mL) at 0° C. under nitrogen, and the resulting mixture was stirred at ambient temperature for 30 minutes. Benzyl bromide (345 mg, 2 mmol) was then added dropwise to the above mixture at 0° C. The resulting mixture was stirred at ambient temperature for 6 hours. Ammonium chloride solution was added carefully to quench the reaction at 0° C. The mixture was extracted with DCM. The combined extracts were washed with saturated ammonium chloride solution, water and brine, dried over sodium sulfate, and evaporated in vacuo to give a brown oil, which was purified by chromatography on silica gel eluting with EtOAc-Hexane (5:95) to give the title compound (421 mg); 1H-NMR (CDCl3): δ 10.53 (1H, s), 7.96 (1H, s), 7.41-7.25 (7H, m), 7.08-6.99 (2H, m), 4.57 (2H, s), 4.33-4.27 (2H, q), 3.48 (2H, m), 3.01 (2H, m), 1.36 (3H, t); MS (ES): 347 (MH+).

1. stirringThe resulting mixture was stirred at ambient temperature for 6 hours
2. customto quench
3. customthe reaction at 0° C
4. extractionThe mixture was extracted with DCM
5. washThe combined extracts were washed with saturated ammonium chloride solution, water and brine
6. dry with materialdried over sodium sulfate
7. customevaporated in vacuo
8. customto give a brown oil, which
9. customwas purified by chromatography on silica gel eluting with EtOAc-Hexane (5:95)

ORD-Eintrag

ord-3b6b450c190647be8e378546c1cf273d

Quelldatensatz

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08133992B2