A kind of synthetic method of 3 cyanoindole compound
A synthesis method and a cyanoindole technology are applied in the field of synthesis of 3-cyanoindole compounds, can solve the problems of harsh reaction conditions, high toxicity of raw materials, narrow substrate range and the like, and achieves easy operation and wide application range. , the effect of avoiding waste of resources
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Embodiment 1
[0011]
[0012] Add 1a (0.5 mmol, 170 mg), 2a (1 mmol, 106 mg), cuprous iodide (0.05 mmol, 9.5 mg), triethylenediamine (0.1 mmol, 11.2 mg) into a 25 mL reaction tube, Trimethylacetic acid (0.5 mmol, 51 mg) and N,N-dimethylformamide (1.5 mL), then concentrated aqueous ammonia (21 mmol, 1.5 mL) was added. Heated to 80°C under air, stirred for 24 hours, quenched the reaction by adding 5 mL of saturated ammonium chloride solution, extracted with ethyl acetate (10 mL × 2), and then washed the organic phase with water and saturated brine successively, and anhydrous Na2SO4 dried. Filtration, spin-drying, and silica gel column separation (petroleum ether / ethyl acetate=5 / 1) gave the white solid product 2-phenyl-3-cyanindole 3a (67 mg, 62%). The characterization data of this compound are as follows: 1 H NMR (400 MHz, CDCl 3 ) δ: 7.26-7.33 (m, 2H), 7.44-7.53 (m, 4H),7.74-7.76 (m, 1H), 7.90 (q, J = 8.0 Hz, 2H), 9.14 (s, 1H). 13 C NMR (100 MHz, CDCl 3 ) δ: 83.9, 111.8, 117.0, 119...
Embodiment 2
[0014] According to the method described in Example 1, 1a (0.5 mmol, 170 mg), 2a (1 mmol, 106 mg), cuprous iodide (0.05 mmol, 9.5 mg), triethylenediamine were added to a 25 mL reaction tube (0.1 mmol, 11.2 mg), trimethylacetic acid (0.5 mmol, 51 mg) and N,N-dimethylformamide (1.5 mL), then concentrated ammonia (21 mmol, 1.5 mL) was added. After heating to 100°C under air and stirring for 24 hours, the product 2-phenyl-3-cyanindole 3a (63 mg, 58%) was obtained.
Embodiment 3
[0016] According to the method described in Example 1, 1a (0.5 mmol, 170 mg), 2a (1 mmol, 106 mg), cuprous iodide (0.05 mmol, 9.5 mg), triethylenediamine were added to a 25 mL reaction tube (0.1 mmol, 11.2 mg), trimethylacetic acid (0.5 mmol, 51 mg) and dimethyl sulfoxide (1.5 mL), then concentrated ammonia (21 mmol, 1.5 mL) was added. After heating to 80°C under air and stirring for 24 hours, the product 2-phenyl-3-cyanindole 3a (65 mg, 60%) was obtained.
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