A kind of preparation method of gamma-carboline derivative
A derivative and carboline technology, which is applied in the field of preparation of γ-carboline derivatives, can solve the problems of rare regioselectivity schemes and low regioselectivity, and achieves a wide range of substrate adaptability and cheap and easy-to-obtain raw materials. , the effect of mild reaction conditions
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Embodiment 1
[0031]
[0032] At room temperature, 0.1 mmol 1-(1-methyl-1H-indol-3-yl)ethan-1-one-O-methyloxime, 0.0025 mmol [Cp * RhCl 2 ] 2 , 0.01mmolAgSbF 6 , 1 mL of TFE, then 0.15 mmol of trimethyl(phenylethynyl)silane was added and the tube was sealed. The reaction was quenched by stirring at 120°C for 24 hours, then the mixture was cooled to room temperature and concentrated under reduced pressure to obtain the crude product. Finally, it was washed with a mixed eluent of petroleum ether and ethyl acetate, and the corresponding γ-carboline derivative was obtained by flash column chromatography (silica gel column), 22 mg of white solid, and the yield was 79%.
[0033] 1 H NMR (500MHz, CDCl 3)δ8.27(s,1H),8.22(d,J=7.9Hz,1H),7.56-7.52(m,1H),7.51-7.44(m,5H),7.42-7.36(m,2H),3.42 (s,3H),3.11(s,3H). 13 C NMR (126MHz, CDCl 3 )δ152.56,145.57,142.58,141.78,137.32,130.52,128.34,127.93,126.25,122.56,122.15,120.77,119.65,117.89,109.12,32.49,24.01.HR-MS(ESI)[M+H] + m / z calcd for C 19 H ...
Embodiment 2
[0035]
[0036] At room temperature, 0.1 mmol 1-(1,5-dimethyl-1H-indol-3-yl)ethan-1-one-O-methyloxime, 0.0025 mmol [ Cp * RhCl 2 ] 2 , 0.01mmolAgSbF 6 , 1 mL of TFE, then 0.15 mmol of trimethyl(phenylethynyl)silane was added and the tube was sealed. The reaction was quenched by stirring at 120°C for 24 hours, then the mixture was cooled to room temperature and concentrated under reduced pressure to obtain the crude product. Finally, it was washed with a mixed eluent of petroleum ether and ethyl acetate, and the corresponding γ-carboline derivative was obtained by flash column chromatography (silica gel column) (white solid 20 mg, yield 70%).
[0037] 1 H NMR (600MHz, CDCl 3 )δ8.23(s,1H),8.00(s,1H),7.51-7.43(m,5H),7.37-7.34(m,1H),7.29(d,J=8.3Hz,1H),3.39(s ,3H),3.10(s,3H),2.59(s,3H). 13 C NMR (151MHz, CDCl 3 )δ152.48,145.33,142.70,140.10,137.37,130.52,130.14,128.31,127.87,127.53,122.61,122.27,119.59,117.73,108.80,32.52,24.06,21.72.HR-MS(ESI[M+72)] + m / zcalcd for C ...
Embodiment 3
[0039]
[0040] At room temperature, 0.1 mmol of 1-(5-methoxy-1-methyl-1H-indol-3-yl)ethan-1-one-O-methyloxime was sequentially added to a 10 mL Schrock reaction tube, 0.0025mmol[Cp * RhCl 2 ] 2 , 0.01mmol 1mL AgSbF 6 , TFE, then 0.15 mmol of trimethyl(phenylethynyl)silane was added and the tube was sealed. Stir at 120°C for 24 hours. The reaction was quenched, then the mixture was cooled to room temperature and concentrated under reduced pressure to give the crude product. Finally, it was washed with a mixed eluent of petroleum ether and ethyl acetate, and the corresponding γ-carboline derivative was obtained by flash column chromatography (silica gel column) (white solid 24 mg, yield 80%).
[0041] 1 H NMR (600MHz, CDCl 3 )δ8.22(s,1H),7.70(d,J=2.4Hz,1H),7.51-7.43(m,5H),7.31(d,J=8.8Hz,1H),7.17(dd,J=8.8 ,2.5Hz,1H),3.96(s,3H),3.39(s,3H),3.09(s,3H). 13 C NMR (151MHz, CDCl 3 )δ154.79,152.55,145.40,142.97,137.29,136.79,130.51,128.34,127.91,122.68,119.70,117.82,114.59,...
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