3-cyan substituted indole compound and synthetic method thereof
A technology of indole compound and cyano group substitution, which is applied in the direction of organic chemistry, can solve the problems of high substrate requirements, complicated reaction steps, and difficulty in obtaining 3-position cyanolated products, so as to avoid metal cyanides and conditions Moderate, easy-to-operate effect
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Embodiment 1
[0044] Example 1: 1-phenyl-1 H - Preparation of indole-3-cyano
[0045] 1-phenyl-1 H -Indole-3-cyano group adopts the following steps: 1. Add 9.7 grams of 1-phenyl-1 in a 250 ml round bottom flask H - Indole, 560 mg of palladium acetate, 43 g of additives, 12.5 g of tert-butylisonitrile, 150 ml of N,N-dimethylformamide, heated to 130°C. Track the reaction with thin layer chromatography, to the reaction raw material 1-phenyl-1 H -Indole disappears; 2. After the reaction is finished, add 3 N ammonia solution to the system, extract the product with ethyl acetate, remove the solvent with a rotary evaporator after drying, and obtain the crude product; 3. Column chromatography (petroleum ether) for the crude product : ethyl acetate = 6 : 1) purification to obtain 8.1 g of 1-phenyl-1 H -Indole-3-cyano, yield 74%. Melting point: 120-121°C.
[0046] IR (KBr, cm -1 ): 2223, 1599, 1539, 1501, 1458, 1224, 736, 694.
[0047] 1 H NMR (CDCl 3 , 500 MHz): δ = 7.85-7....
Embodiment 2
[0050] Example 2: 1-(4-fluoro-phenyl)-1 H - Preparation of indole-3-cyano
[0051] 1-(4-fluoro-phenyl)-1 H -Indole-3-cyano uses the following steps: ①Add 10.5 grams of 1-(4-fluoro-phenyl)-1 to a 250 ml round bottom flask H - Indole, 560 mg of palladium acetate, 43 g of additives, 12.5 g of tert-butylisonitrile, 150 ml of N,N-dimethylformamide, heated to 130°C. Track the reaction with thin layer chromatography until the reaction raw material 1-(4-fluoro-phenyl)-1 H -Indole disappears; 2. After the reaction is finished, add 3 N ammonia solution to the system, extract the product with ethyl acetate, remove the solvent with a rotary evaporator after drying, and obtain the crude product; 3. Column chromatography (petroleum ether) for the crude product : Ethyl acetate = 6: 1) purification to obtain 7.4 g of 1-(4-fluoro-phenyl)-1 H -Indole-3-cyano, yield 63%. Melting point: 164-167°C.
[0052] IR (KBr, cm -1 ): 2227, 1539, 1515, 1460, 1215, 837, 740.
[0053] 1 H N...
Embodiment 3
[0058] Example three: 1-(4-methoxy-phenyl)-1 H - Preparation of indole-3-cyano
[0059] 1-(4-Methoxy-phenyl)-1 H -Indole-3-cyano uses the following steps: ①Add 11.1 grams of 1-(4-methoxy-phenyl)-1 to a 250-ml round-bottomed flask H - Indole, 560 mg of palladium acetate, 43 g of additives, 12.5 g of tert-butylisonitrile, 150 ml of N,N-dimethylformamide, heated to 130°C. Track the reaction with thin-layer chromatography until the reaction raw material 1-(4-methoxy-phenyl)-1 H -Indole disappears; 2. After the reaction is finished, add 3 N ammonia solution to the system, extract the product with ethyl acetate, remove the solvent with a rotary evaporator after drying, and obtain the crude product; 3. Column chromatography (petroleum ether) for the crude product : Ethyl acetate = 6: 1) purification to obtain 4.6 grams of 1-(4-methoxy-phenyl)-1 H -Indole-3-cyano, yield 36%. Melting point: 126-129°C.
[0060] IR (KBr,cm –1 ): 2219, 1535, 1513, 1458, 1245, 1219, 1028, 836,...
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