Reaction #66228

Reaction equation

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

Na2CO3

→

title compound

Yield 91.1%

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

Yield 91.1%

Solvents

DCM

EtOH

Conditions

Workup

1. 1
   Temperaturereflux under N2 for 3.5 hours
2. 2
   Washwashed with brine
3. 3
   ExtractionThe aqueous phase was extracted with DCM (10 mL) twice
4. 4
   DryingThe combined organic phase was dried over Na2SO4
5. 5
   Concentrationconcentrated
6. 6
   OtherThe crude product was purified by flash chromatograph on silica gel
7. 7
   Washeluting with EtOAc-hexane (0-30%)

Procedure

To a stirred solution of 3-(4-fluorobenzoyl)-8-(3-methoxyphenyl)-1,2,3,6-tetrahydroazepino[4,5-b]indole-5-carboxylic acid ethyl ester (48 mg, 0.10 mmol) in 2 mL of EtOH was added 0.30 mL of 1M Na2CO3 solution at ambient temperature. The reaction mixture was heated at 93° C. reflux under N2 for 3.5 hours and samples monitored by LC-MS. The solution was diluted with DCM (10 mL), washed with brine. The aqueous phase was extracted with DCM (10 mL) twice. The combined organic phase was dried over Na2SO4 and concentrated. The crude product was purified by flash chromatograph on silica gel, eluting with EtOAc-hexane (0-30%) to yield the title compound (33 mg) as a yellow solid; 1H-NMR (CDCl3): δ 10.46 (1H, s), 7.73 (1H, d), 7.47 (1H, d), 7.37 (1H, d), 7.26 (2H, m), 7.12 (1H, m), 7.00 (1H, m), 6.79 (1H, m), 5.25 (1H, s), 4.21 (2H, m), 3.80 (3H, s), 3.55 (2H, m), 3.11 (2H, m), 1.26 (3H, t). MS (ESI): 363 (MH+).

Source