Reaktion #66235

Reaktionsgleichung

N,N-dimethylethylenediamine

Triphosgene

3-(4-fluorobenzoyl)-8-hydroxy-1,1-dimethyl-1,2,3,6-tetrahydroazepino[4,5-b]indole-5-carboxylic acid ethyl ester

diisopropylethylamine

→

title compound

Ausbeute 28.9%

8-(2-Dimethylamino-Ethylcarbamoyloxy)-3-(4-Fluorobenzoyl)-1,1-Dimethyl-1,2,3,6-Tetrahydroazepino[4,5-b]Indole-5-Carboxylic Acid Ethyl Ester

Ausbeute 28.9%

Lösungsmittel

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe mixture was stirred at ambient temperature overnight
2. 2
   SonstigeThe solvents were removed in vacuo
3. 3
   Sonstigethe residue was purified by preparative reverse-phase HPLC

Vorschrift

Triphosgene (58 mg, 0.195 mmol) was added to a stirred solution of 3-(4-fluorobenzoyl)-8-hydroxy-1,1-dimethyl-1,2,3,6-tetrahydroazepino[4,5-b]indole-5-carboxylic acid ethyl ester (49 mg, 0.116 mmol) and diisopropylethylamine (0.8 mL, 4.01 mmol) in dry DCM (10 mL) at 0° C. under N2. The resulting mixture was stirred at ambient temperature for 1.5 hours, and N,N-dimethylethylenediamine (0.1 mL, 0.91 mmol) was added. The mixture was stirred at ambient temperature overnight. The solvents were removed in vacuo, and the residue was purified by preparative reverse-phase HPLC to give the title compound (18 mg); 1H-NMR (CDCl3): 10.63 (1H, s), 7.76 (2H, m), 7.63-7.60 (2H, m), 7.16-7.11 (3H, m), 6.88-6.86 (1H, dd), 5.61 (1H, t), 4.24 (2H, q), 4.10 (2H, brs), 3.37 (2H, m), 2.48 (2H, m), 2.27 (6H, s), 1.59 (6H, s), 1.24 (3H, t); MS (ES): 537 (MH+).

Quelle