A method for synthesizing bis-indolylmethane derivatives
A technology of bisindolylmethane and indole derivatives, which is applied in the direction of organic chemistry, etc., can solve the problems of high toxicity of raw material aldehydes, easy to deteriorate, and difficult to store for a long time, and achieves the effect of broad development prospects.
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Embodiment 1
[0025] Example 1: Bis(1H-indole)methane
[0026] Di(1H-indol-3-yl)methane
[0027]
[0028] Under nitrogen, indole (234 mg, 2 mmol), [Cp*IrCl 2 ] 2 (3.2 mg , 0.004 mmol, 0.2 mol%), potassium tert-butoxide (224 mg, 2 mmol, 1 equiv.) and methanol (1 ml, 790 mg, 24.7 mmol, 12.4 equiv.) were sequentially added to 25 ml Schlenk reaction in the bottle. The reaction mixture was at 150 o After 12 h at C, cool to room temperature. The solvent was removed by rotary evaporation, and then the pure target compound was obtained by column chromatography (developing solvent: ethyl acetate / petroleum ether), yield: 86%
[0029] 1 H NMR (500 MHz, DMSO-d 6 ) δ 10.73 (br s, 2H, 2xNH), 7.52 (d, J = 7.7 Hz, 2H, ArH), 7.31 (d, J = 8.0 Hz, 2H, ArH), 7.13 (s, 2H, ArH), 7.02 (t, J = 7.4 Hz, 2H, ArH), 6.91 (t, J = 7.4 Hz, 2H, ArH), 4.12 (s, 2H, CH 2 ); 13 C NMR (125 MHz, DMSO-d 6 ) δ 136.4, 127.2, 122.7, 120.7, 118.7, 118.0, 114.2, 111.3, 20.9.
Embodiment 2
[0030] Example 2: Bis(4-methyl-1H-indole)methane
[0031] bis(4-methyl-1H-indol-3-yl)methane
[0032]
[0033] Under nitrogen, 4-methylindole (262 mg, 2 mmol), [Cp*IrCl 2 ] 2 (3.2 mg, 0.004 mmol, 0.2 mol%), potassium tert-butoxide (224 mg, 2 mmol, 1 equiv.) and methanol (1 ml) were sequentially added to a 25 ml Schlenk reaction flask. The reaction mixture was at 150 o After 12 h at C, cool to room temperature. The solvent was removed by rotary evaporation, and then the pure target compound was obtained by column chromatography (developing solvent: ethyl acetate / petroleum ether), yield: 81%
[0034] 1 H NMR (500 MHz, CDCl 3 ) δ 7.82 (br s, 2H, 2xNH), 7.18 (d, J = 8.2 Hz, 2H, ArH), 7.07 (t, J = 7.7 Hz, 2H, ArH), 6.84 (d, J = 7.2 Hz, 2H , ArH), 6.68 (s, 2H, ArH), 4.55 (s, 2H, CH 2 ), 2.65 (s, 6H, 2xCH 3 ); 13 C NMR (125 MHz, CDCl 3 ) δ 137.0, 131.3, 125.9, 122.9, 122.0, 120.7, 117.5, 108.9, 25.7, 20.1.
Embodiment 3
[0035] Example 3: Bis(5-methyl-1H-indole)methane
[0036] bis(5-methyl-1H-indol-3-yl)methane
[0037]
[0038] Under nitrogen, 5-methylindole (262 mg, 2 mmol), [Cp*IrCl 2 ] 2(3.2 mg, 0.004 mmol, 0.2 mol%), potassium tert-butoxide (224 mg, 2 mmol, 1 equiv.) and methanol (1 ml) were sequentially added to a 25 ml Schlenk reaction flask. The reaction mixture was at 150 o After 12 h at C, cool to room temperature. The solvent was removed by rotary evaporation, and then the pure target compound was obtained by column chromatography (developing solvent: ethyl acetate / petroleum ether), yield: 85%
[0039] 1 H NMR (500 MHz, CDCl 3 ) δ 7.78 (br s, 2H, 2xNH), 7.41 (s, 2H, ArH), 7.24 (d, J = 8.3 Hz, 2H, ArH), 7.02 (d, J = 7.9 Hz, 2H, ArH), 6.87 (d, J = 5.1 Hz, 2H, ArH), 4.18 (s, 2H, CH 2 ), 2.43 (s, 6H, 2xCH 3 ); 13 C NMR (125 MHz, CDCl 3 ) δ 134.8, 128.3, 127.8, 123.4, 122.4, 118.8, 115.2, 110.7, 21.5, 21.1; HRMS-EI (70 eV) m / z calcd for C 19 h 18 N 2 Na [M+Na] + 297....
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