Reacción #66207

Ecuación de reacción

9-bromo-1,2,3,6-tetrahydroazepino[4,5-b]indole-5-carboxylic acid ethyl ester

4-methoxyphenylboronic acid

Na2CO3

→

title compound

Rendimiento 62.5%

9-(4-Methoxyphenyl)-1,2,3,6-Tetrahydroazepino[4,5-b]Indole-5-Carboxylic Acid Ethyl Ester

Rendimiento 62.5%

Disolventes

DME EtOH

DCM

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadowashed with brine
2. 2
   ExtracciónThe aqueous phase was extracted with DCM (20 mL) twice
3. 3
   SecadoThe combined organic phase was dried over Na2SO4
4. 4
   Concentraciónconcentrated
5. 5
   OtroThe crude product was purified by flash chromatograph on silica gel
6. 6
   Lavadoeluting with EtOAc-hexane (0-30%)

Procedimiento

To a stirred solution of 9-bromo-1,2,3,6-tetrahydroazepino[4,5-b]indole-5-carboxylic acid ethyl ester (0.20 g, 0.60 mmol), (o-tolyl)3P (0.19 g, 0.6 mmol) and 4-methoxyphenylboronic acid (0.23 g, 1.5 mmol) in DME/EtOH (1:1, 12 mL) was added 2.1 mL of 1M Na2CO3 solution and Pd(OAc)2 (27 mg) at ambient temperature. The reaction mixture was heated at 80° C. under N2 for 1 hour and monitored by LC-MS. The solution was diluted with DCM (20 mL), and washed with brine. The aqueous phase was extracted with DCM (20 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 (0.136 g) as a light yellow solid; 1H-NMR (CDCl3): δ 10.41 (1H, s), 7.73 (1H, d), 7.50 (3H, m), 7.29 (1H, d), 7.21 (1H, d), 6.90 (2H, m), 5.23 (1H, s), 4.20 (2H, dd), 3.76 (3H, s), 3.55 (2H, m), 3.12 (2H, m), 1.26 (3H, t); MS (ESI): 363 (MH+).

Fuente