تفاعل #66207

معادلة التفاعل

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

4-methoxyphenylboronic acid

Na2CO3

→

title compound

المردود 62.5%

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

المردود 62.5%

المذيبات

DME EtOH

DCM

ظروف التفاعل

المعالجة

1. 1
   غسيلwashed with brine
2. 2
   استخلاصThe aqueous phase was extracted with DCM (20 mL) twice
3. 3
   تجفيفThe combined organic phase was dried over Na2SO4
4. 4
   تركيزconcentrated
5. 5
   أخرىThe crude product was purified by flash chromatograph on silica gel
6. 6
   غسيلeluting with EtOAc-hexane (0-30%)

الإجراء التجريبي

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+).

المصدر