A synthesizing method of 3-substituted phenyl indole compounds
A technology of a phenylindole compound and a synthesis method, which is applied in directions such as organic chemistry, can solve the problems of low reaction yield and difficulty in obtaining reaction raw materials, and achieves the effects of reducing reaction steps, low synthesis cost and high selectivity
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Embodiment 1
[0035] Embodiment 1: the synthesis of 3-phenylindole
[0036] Reaction equation:
[0037] Weigh indole (92.6 mg, 0.7908 mmol), potassium carbonate (262.3 mg, 1.898 mmol) into a Schlenk bottle, then add bromobenzene (0.1 ml, 0.9496 mmol) and 2 ml of dioxane, in After stirring for 15 minutes under the protection of nitrogen, 20.1 mg of POPd (0.04000 mmol, 5 mol%) was added, heated and stirred vigorously, and refluxed for 24 hours. The reaction was tracked by high performance liquid chromatography and TLC. After stopping the reaction, the reaction solution was cooled to room temperature, and ether (10 mL) and water (10 mL) were added thereto, transferred to a separatory funnel, the oil layer was separated, and the water layer was extracted with ethyl acetate (3×10 mL). The enriched organic layer was washed with saturated brine (20 mL), dried over anhydrous magnesium sulfate, and left standing in an Erlenmeyer flask. Filter and remove the solvent by rotary evaporation. The crud...
Embodiment 2
[0042] Embodiment 2: the synthesis of 3-(4-methylphenyl)indole
[0043] Indole (97.0 mg, 0.8282 mmol), p-bromotoluene (170.0 mg, 0.9939 mmol), potassium carbonate (228.9 mg, 1.6564 mmol), POPd (20.8 mg, 0.04140 mmol, 5 mol%) and 2 ml Toluene was added into the reactor, and the experimental procedure was as described above to obtain 100.7 mg of light yellow flaky crystals with a melting point of 86.2-87.5° C. and an isolated yield of 53.9%.
[0044] 1 H NMR (500MHz, CDCl 3 )δ: 8.24(s, 1H, 1 # H), 7.95-7.93 (d, 1H, J=8.1Hz, 5 # H), 7.59-7.58 (d, 2H, J=8.2Hz, 7 # H), 7.45-7.43 (d, 1H, J=8.2Hz, 2 # H), 7.36-7.35 (d, 1H, J=2.4Hz, 6 # H), 7.29-7.20 (m, 3H, 3 # and 8 # H), 7.17-7.15 (t, 1H, J=8.2Hz, 4 # H);
[0045] IR (cm -1 )3440(υ NH ), 2995 (υ as CH ), 2872 (υ s CH ), 1640, 1550, 1460 (υ C＝C ), 1440(δ as CH ), 810, 740 (γ 面外＝C-H );
[0046] MS(m / z)208.0[M+1] + .
[0047]
Embodiment 3
[0048] Embodiment 3: the synthesis of 3-(4-nitrophenyl) indole
[0049] Indole (50.0 mg, 0.4268 mmol), p-bromonitrobenzene (103.5 mg, 0.5122 mmol), potassium carbonate (118.0 mg, 0.8536 mmol), POPd (10.7 mg, 0.02134 mmol, 5 mol%) and 2 milliliters of toluene was added into the reactor, and the experimental procedure was as described above to obtain 50.9 milligrams of a brownish-yellow solid with a melting point of 142.5-144.2° C. and an isolated yield of 48.0%.
[0050] 1 H NMR (500MHz, CDCl 3 )δ: 8.52(s, 1H, 1 # H), 8.32-8.30 (d, 2H, J=8.9Hz, 7 # H), 7.98-7.96 (d, 1H, J=8.0Hz, 5 # H), 7.84-7.83 (d, 2H, J=8.8Hz, 8 # H), 7.55(s, 1H, 6 # H), 7.50-7.49 (d, 1H, J=8.1Hz, 2 # H), 7.34-7.27 (m, 2H, 3 # and 4 # H);
[0051] IR (cm -1 )3420(υ NH ), 1505 (υ as NO2 ), 1340 (υ s NO2 ), 1600, 1540 (υ C＝C ), 860(υ C-N ), 810 (γ 面外＝C-H );
[0052] MS(m / z)239.1[M+1] + .
[0053]
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