CN111892593B - 8-methoxy-5H-pyrido [4,3-b ] indole and synthetic method thereof - Google Patents
8-methoxy-5H-pyrido [4,3-b ] indole and synthetic method thereof Download PDFInfo
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Abstract
The invention belongs to the technical field of organic synthesis, and relates to 8-methoxy-5H-pyrido [4,3-b ] indole and a synthesis method thereof. The synthesis method provided by the invention comprises the following steps: 1- (4-methoxyphenyl) hydrazine is used as a raw material, and the 8-methoxy-5H-pyrido [4,3-b ] indole is prepared by five-step reaction of ketoamine condensation, sulfonylation, active hydrogen protection, elimination and hydrolysis reaction, and has the advantages of simple synthetic route, low cost and high efficiency.
Description
Technical Field
The invention belongs to the technical field of organic synthesis, and relates to indole derivative 8-methoxy-5H-pyrido [4,3-b ] indole and a synthesis method thereof.
Background
Indole derivatives are an important class of nitrogen heterocyclic compounds, widely exist in the whole natural world and often have important physiological and pharmacological activities. For example, indole derivatives are important pharmaceutical intermediates useful in the synthesis of many drugs. In addition, indole is used as a fine chemical product intermediate and has wide application in the fields of catalysts, medicines, pesticides and the like. The synthesis of indole derivatives is therefore of great importance.
Disclosure of Invention
The invention aims to provide a compound 8-methoxy-5H-pyrido [4,3-b ] indole and a synthesis method thereof, wherein the compound can be used as a medical intermediate, and the synthesis method is simple and has high yield.
In order to achieve the purpose, the technical scheme of the invention is as follows:
a compound is 8-methoxy-5H-pyrido [4,3-b ] indole, and the molecular structure is shown in formula 1:
the invention also provides a synthesis method of the compound, which takes 1- (4-methoxyphenyl) hydrazine as a raw material to synthesize the compound through five-step reaction of ketoamine condensation, sulfonylation, active hydrogen protection, elimination and hydrolysis reaction, wherein the synthesis route is shown as the following formula:
the synthesis method comprises the following steps:
s1, adding N-tert-butyloxycarbonyl-4-piperidone into a mixed solvent of absolute ethanol and hydrochloric acid, adding 1- (4-methoxyphenyl) hydrazine, controlling the reaction temperature to be 80-90 ℃, and reacting for 12 hours to obtain 8-methoxy-2, 3,4, 5-tetrahydro-1H-pyrido [4,3-b ] indole hydrochloride;
s2, adding 8-methoxy-2, 3,4, 5-tetrahydro-1H-pyrido [4,3-b ] indole hydrochloride obtained in the step S1 into a mixed solvent of dichloromethane and water, then adding an inorganic base, cooling to 15 ℃, adding benzenesulfonyl chloride, heating to room temperature, and reacting for 12 hours to obtain 8-methoxy-2- (benzenesulfonyl) -2,3,4, 5-tetrahydro-1H-pyrido [4,3-b ] indole;
s3, adding sodium hydride into N2Adding into DMF under atmosphere, cooling to 15 deg.C, slowly adding 8-methoxy-2- (benzenesulfonyl) -2,3,4, 5-tetrahydro-1H-pyrido [4,3-b ] obtained in step S2]Indole is added dropwise after the reaction for 0.5H, the reaction temperature is controlled, the reaction is carried out for 12H, and 8-methoxy-2- (phenylsulfinyl) -5- (phenylsulfonyl) -2,3,4, 5-tetrahydro-1H-pyrido [4,3-b ] is obtained]Indole;
s4, adding the 8-methoxy-2- (phenylsulfinyl) -5- (phenylsulfonyl) -2,3,4, 5-tetrahydro-1H-pyrido [4,3-b ] indole obtained in the step S3 into 1, 4-dioxane, adding selenium dioxide, controlling the reaction temperature to be 100 ℃ and 110 ℃, and reacting for 3d to obtain 8-methoxy-5- (phenylsulfonyl) -5H-pyrido [4,3-b ] indole;
s5, adding the 8-methoxy-5- (benzenesulfonyl) -5H-pyrido [4,3-b ] indole obtained in the step S4 into a mixed solvent of tetrahydrofuran and water, then adding an inorganic base, controlling the reaction temperature to be 90-100 ℃, and reacting for 12H to obtain the 8-methoxy-5H-pyrido [4,3-b ] indole.
Further, the reaction temperature in the step S2 is 20 to 30 ℃.
Further, the inorganic base is one of sodium carbonate, potassium carbonate, sodium bicarbonate and potassium bicarbonate.
Further, the reaction temperature in the step S3 is 20 to 30 ℃.
Compared with the prior art, the invention provides a new medical intermediate, and the synthesis method provided by the invention has the advantages of simple synthesis path, low cost and high efficiency.
Detailed description of the invention
The following detailed description will provide specific embodiments of the present invention. These embodiments are merely illustrative and not intended to limit the scope or the principles of the invention, which is defined by the claims and includes obvious modifications and variations based thereon.
Example 1
Synthesis of S1, 8-methoxy-2, 3,4, 5-tetrahydro-1H-pyrido [4,3-b ] indole hydrochloride:
132.8g 132.8g N-tert-butoxycarbonyl-4-piperidone and 270ml hydrochloric acid were dissolved in 1.4L absolute ethanol in a 3L four-necked flask, and 92.1g1- (4-methoxyphenyl) hydrazine was added thereto under magnetic stirring, and the mixture was heated to 80 ℃ to react for 12 hours. The raw materials are completely reacted by liquid chromatography-mass spectrometry, redundant solvent is evaporated, the mixture is filtered, a filter cake is washed by absolute ethyl alcohol, dried and concentrated to obtain 141.2g of 8-methoxy-2, 3,4, 5-tetrahydro-1H-pyrido [4,3-b ] indole hydrochloride solid, and the yield is 88.4%.
Synthesis of S2, 8-methoxy-2- (benzenesulfonyl) -2,3,4, 5-tetrahydro-1H-pyrido [4,3-b ] indole:
140g of 8-methoxy-2, 3,4, 5-tetrahydro-1H-pyrido [4,3-b ] indole hydrochloride is dissolved in 1.2L of dichloromethane and 1.2L of deionized water in a 3L four-neck flask, 203g of potassium carbonate is added, the temperature is reduced to about 15 ℃ under mechanical stirring, 114.3g of benzenesulfonyl chloride is slowly added dropwise, and the temperature is naturally raised to room temperature after the dropwise addition for reaction for 12 hours. After completion of the reaction of the starting materials was analyzed by thin layer chromatography, the reaction system was filtered, and the cake was washed 3 times with water (3X 0.35L). Drying to obtain 155.8g of 8-methoxy-2- (benzenesulfonyl) -2,3,4, 5-tetrahydro-1H-pyrido [4,3-b ] indole solid with the yield of 77.5 percent.
Synthesis of S3, 8-methoxy-2- (phenylsulfinyl) -5- (phenylsulfonyl) -2,3,4, 5-tetrahydro-1H-pyrido [4,3-b ] indole:
to a 3L reaction flask was added 1.5L of DMF in N2Adding 12.6g of sodium hydride under protection, cooling to 15 ℃, and slowly adding 150g of 8-methoxy-2- (benzenesulfonyl) -2,3,4, 5-tetrahydro-1H-pyrido [4,3-b ]]Indole, and reacting for 30 min. 92.9g of benzenesulfonyl chloride were then added dropwise,naturally raising the temperature to 25 ℃ and reacting for 12 h. Thin layer chromatography analysis of raw materials reaction completely, slowly adding 3L ice water into the system, stirring for 30min, filtering, washing the filter cake with water, drying to obtain 8-methoxy-2- (phenylsulfinyl) -5- (phenylsulfonyl) -2,3,4, 5-tetrahydro-1H-pyrido [4,3-b ]]Indole solid 203.3g, yield 99.6%.
Synthesis of S4, 8-methoxy-5- (benzenesulfonyl) -5H-pyrido [4,3-b ] indole:
200g of 8-methoxy-2- (phenylsulfinyl) -5- (phenylsulfonyl) -2,3,4, 5-tetrahydro-1H-pyrido [4,3-b ] indole was dissolved in 4L of 1, 4-dioxane in a 5L four-necked flask, 238.2g of selenium dioxide was added with mechanical stirring, and the mixture was heated to 105 ℃ for reaction for 3 d. The thin-layer chromatography analysis shows that the raw materials react completely, the system is cooled to room temperature, the filtration is carried out, and the filtrate is continuously cooled to 14 ℃. Stirring for 30min, filtering, drying, adding 5L of water, adjusting pH to 9 with potassium carbonate, filtering, washing with water once, and drying to obtain 145g of 8-methoxy-5- (benzenesulfonyl) -5H-pyrido [4,3-b ] indole solid with the yield of 100%.
Synthesis of S5, 8-methoxy-5H-pyrido [4,3-b ] indole:
145g of 8-methoxy-5- (benzenesulfonyl) -5H-pyrido [4,3-b ] indole was dissolved in 1.5L of tetrahydrofuran and 1.5L of water in a 5L four-necked flask, and 85.8g of sodium hydroxide was added thereto with mechanical stirring, and the mixture was heated to 90 ℃ to react for 10 hours and 12 hours. Thin-layer chromatography analysis shows that the raw materials react completely, the system is cooled to 40 ℃, the filtration is carried out, the filtrate is concentrated to remove tetrahydrofuran, 2L of water is added, the pulping and the filtration are carried out, the filter cake is washed by 1L of water and dried to obtain 43.2g of 8-methoxy-5H-pyrido [4,3-b ] indole solid, and the yield is 50.8%.
Example 2
Synthesis of S1, 8-methoxy-2, 3,4, 5-tetrahydro-1H-pyrido [4,3-b ] indole hydrochloride:
132.8g 132.8g N-tert-butoxycarbonyl-4-piperidone and 270ml hydrochloric acid were dissolved in 1.4L absolute ethanol in a 3L four-necked flask, and 92.1g1- (4-methoxyphenyl) hydrazine was added thereto under magnetic stirring, and the mixture was heated to 90 ℃ to react for 9 hours. The raw materials are completely reacted by liquid chromatography-mass spectrometry, redundant solvent is evaporated, the mixture is filtered, a filter cake is washed by absolute ethyl alcohol, dried and concentrated to obtain 120.8g of 8-methoxy-2, 3,4, 5-tetrahydro-1H-pyrido [4,3-b ] indole hydrochloride solid, and the yield is 75.6%.
Synthesis of S2, 8-methoxy-2- (benzenesulfonyl) -2,3,4, 5-tetrahydro-1H-pyrido [4,3-b ] indole:
140g of 8-methoxy-2, 3,4, 5-tetrahydro-1H-pyrido [4,3-b ] indole hydrochloride is dissolved in 1.2L of dichloromethane and 1.2L of deionized water in a 3L four-neck flask, 203g of sodium carbonate is added, the temperature is reduced to about 15 ℃ under mechanical stirring, 114.3g of benzenesulfonyl chloride is slowly added dropwise, and the temperature is raised to 30 ℃ after the dropwise addition for reaction for 15 hours. After completion of the reaction of the starting materials was analyzed by thin layer chromatography, the reaction system was filtered, and the cake was washed 3 times with water (3X 0.35L). Drying to obtain 162.1g of 8-methoxy-2- (benzenesulfonyl) -2,3,4, 5-tetrahydro-1H-pyrido [4,3-b ] indole solid with the yield of 80.1%.
Synthesis of S3, 8-methoxy-2- (phenylsulfinyl) -5- (phenylsulfonyl) -2,3,4, 5-tetrahydro-1H-pyrido [4,3-b ] indole:
A3L reaction flask was charged with 1.5LDMF in N2Adding 12.6g of sodium hydride under protection, cooling to 15 ℃, and slowly adding 150g of 8-methoxy-2- (benzenesulfonyl) -2,3,4, 5-tetrahydro-1H-pyrido [4,3-b ]]Indole, and reacting for 30 min. Then 92.9g of benzene sulfonyl chloride is added dropwise, the temperature is raised to 20 ℃, and the reaction is carried out for 15 h. Thin layer chromatography analysis of raw materials reaction completely, slowly adding 3L ice water into the system, stirring for 30min, filtering, washing the filter cake with water, drying to obtain 8-methoxy-2- (phenylsulfinyl) -5- (phenylsulfonyl) -2,3,4, 5-tetrahydro-1H-pyrido [4,3-b ]]Indole solid 196.8g, yield 96.4%.
Synthesis of S4, 8-methoxy-5- (benzenesulfonyl) -5H-pyrido [4,3-b ] indole:
200g of 8-methoxy-2- (phenylsulfinyl) -5- (phenylsulfonyl) -2,3,4, 5-tetrahydro-1H-pyrido [4,3-b ] indole were dissolved in 4L of 1, 4-dioxane in a 5L four-necked flask, 238.2g of selenium dioxide were added with mechanical stirring, and the temperature was raised to 100 ℃ for reaction for 4 d. The thin-layer chromatography analysis shows that the raw materials react completely, the system is cooled to room temperature, the filtration is carried out, and the filtrate is continuously cooled to 14 ℃. Stirring for 30min, filtering, drying, adding 5L of water, adjusting pH to 9 with potassium carbonate, filtering, washing with water once, and drying to obtain 145g of 8-methoxy-5- (benzenesulfonyl) -5H-pyrido [4,3-b ] indole solid with the yield of 100%.
Synthesis of S5, 8-methoxy-5H-pyrido [4,3-b ] indole:
145g of 8-methoxy-5- (benzenesulfonyl) -5H-pyrido [4,3-b ] indole was dissolved in 1.5L of tetrahydrofuran and 1.5L of water in a 5L four-necked flask, and 85.8g of sodium hydroxide was added thereto with mechanical stirring, and the mixture was heated to 95 ℃ to react for 10 hours. Thin-layer chromatography analysis shows that the raw materials react completely, the system is cooled to 40 ℃, the filtration is carried out, the filtrate is concentrated to remove tetrahydrofuran, 2L of water is added, the pulping and the filtration are carried out, the filter cake is washed by 1L of water and dried to obtain 39.5g of 8-methoxy-5H-pyrido [4,3-b ] indole solid, and the yield is 46.5%.
Example 3
Synthesis of S1, 8-methoxy-2, 3,4, 5-tetrahydro-1H-pyrido [4,3-b ] indole hydrochloride:
132.8g 132.8g N-tert-butoxycarbonyl-4-piperidone and 270ml hydrochloric acid were dissolved in 1.4L absolute ethanol in a 3L four-necked flask, and 92.1g1- (4-methoxyphenyl) hydrazine was added under magnetic stirring, and the mixture was heated to 85 ℃ to react for 15 hours. The raw materials are completely reacted by liquid chromatography-mass spectrometry, redundant solvent is evaporated, the mixture is filtered, a filter cake is washed by absolute ethyl alcohol, dried and concentrated to obtain 144.1g of 8-methoxy-2, 3,4, 5-tetrahydro-1H-pyrido [4,3-b ] indole hydrochloride solid, and the yield is 90.2%.
Synthesis of S2, 8-methoxy-2- (benzenesulfonyl) -2,3,4, 5-tetrahydro-1H-pyrido [4,3-b ] indole:
140g of 8-methoxy-2, 3,4, 5-tetrahydro-1H-pyrido [4,3-b ] indole hydrochloride was dissolved in 1.2L of dichloromethane and 1.2L of deionized water in a 3L four-necked flask, 203g of sodium bicarbonate was added, the temperature was reduced to about 15 ℃ with mechanical stirring, 114.3g of benzenesulfonyl chloride was slowly added dropwise, and the temperature was raised to 20 hours after the dropwise addition. After completion of the reaction of the starting materials was analyzed by thin layer chromatography, the reaction system was filtered, and the cake was washed 3 times with water (3X 0.35L). Drying to obtain 141.7g of 8-methoxy-2- (benzenesulfonyl) -2,3,4, 5-tetrahydro-1H-pyrido [4,3-b ] indole solid with the yield of 70.5%.
Synthesis of S3, 8-methoxy-2- (phenylsulfinyl) -5- (phenylsulfonyl) -2,3,4, 5-tetrahydro-1H-pyrido [4,3-b ] indole:
A3L reaction flask was charged with 1.5LDMF in N2Adding 12.6g of sodium hydride under protection, cooling to 15 ℃, and slowly adding 150g of 8-methoxy-2- (benzenesulfonyl) -2,3,4, 5-tetrahydro-1H-pyrido [4,3-b ]]Indole, and reacting for 30 min. Then 92.9g of benzene sulfonyl chloride is added dropwise, the temperature is raised to 30 ℃, and the reaction lasts 10 hours. Thin layer chromatography analysis of raw materials reaction completely, slowly adding 3L ice water into the system, stirring for 30min, filtering, washing the filter cake with water, drying to obtain 8-methoxy-2- (phenylsulfinyl) -5- (phenylsulfonyl) -2,3,4, 5-tetrahydro-1H-pyrido [4,3-b ]]Indole solid 194.3g, yield 95.2%.
Synthesis of S4, 8-methoxy-5- (benzenesulfonyl) -5H-pyrido [4,3-b ] indole:
200g of 8-methoxy-2- (phenylsulfinyl) -5- (phenylsulfonyl) -2,3,4, 5-tetrahydro-1H-pyrido [4,3-b ] indole was dissolved in 4L of 1, 4-dioxane in a 5L four-necked flask, 238.2g of selenium dioxide was added with mechanical stirring, and the mixture was heated to 110 ℃ and reacted for 2.5 d. The thin-layer chromatography analysis shows that the raw materials react completely, the system is cooled to room temperature, the filtration is carried out, and the filtrate is continuously cooled to 14 ℃. Stirring for 30min, filtering, drying, adding 5L of water, adjusting pH to 9 with potassium carbonate, filtering, washing with water once, and drying to obtain 145g of 8-methoxy-5- (benzenesulfonyl) -5H-pyrido [4,3-b ] indole solid with the yield of 100%.
Synthesis of S5, 8-methoxy-5H-pyrido [4,3-b ] indole:
145g of 8-methoxy-5- (benzenesulfonyl) -5H-pyrido [4,3-b ] indole was dissolved in 1.5L of tetrahydrofuran and 1.5L of water in a 5L four-necked flask, and 85.8g of sodium hydroxide was added thereto with mechanical stirring, and the mixture was heated to 100 ℃ to react for 9 hours. Thin-layer chromatography analysis shows that the raw materials react completely, the system is cooled to 40 ℃, the filtration is carried out, the filtrate is concentrated to remove tetrahydrofuran, 2L of water is added, the pulping and the filtration are carried out, the filter cake is washed by 1L of water and dried to obtain 51.3g of 8-methoxy-5H-pyrido [4,3-b ] indole solid, and the yield is 60.3%.
While there have been shown and described what are at present considered the fundamental principles and essential features of the invention and its advantages, it will be apparent to those skilled in the art that the invention is not limited to the details of the foregoing exemplary embodiments, but is capable of other specific forms without departing from the spirit or essential characteristics thereof. The present embodiments are therefore to be considered in all respects as illustrative and not restrictive, the scope of the invention being indicated by the appended claims rather than by the foregoing description, and all changes which come within the meaning and range of equivalency of the claims are therefore intended to be embraced therein. Although embodiments of the present invention have been shown and described, it will be appreciated by those skilled in the art that changes, modifications, substitutions and alterations can be made in these embodiments without departing from the principles and spirit of the invention, the scope of which is defined in the appended claims and their equivalents.
Claims (4)
1. A synthetic method of a compound with a structure shown as a formula I is 8-methoxy-5H-pyrido [4,3-b ] indole, and is characterized in that 1- (4-methoxyphenyl) hydrazine is used as a raw material to synthesize the compound through five-step reaction, wherein the synthetic route is as follows:
the synthesis method comprises the following steps:
s1, adding N-tert-butyloxycarbonyl-4-piperidone into a mixed solvent of absolute ethanol and hydrochloric acid, adding 1- (4-methoxyphenyl) hydrazine, controlling the reaction temperature to be 80-90 ℃, and reacting for 12 hours to obtain 8-methoxy-2, 3,4, 5-tetrahydro-1H-pyrido [4,3-b ] indole hydrochloride;
s2, adding 8-methoxy-2, 3,4, 5-tetrahydro-1H-pyrido [4,3-b ] indole hydrochloride obtained in the step S1 into a mixed solvent of dichloromethane and water, then adding an inorganic base, cooling to 15 ℃, adding benzenesulfonyl chloride, heating to room temperature, and reacting for 12 hours to obtain 8-methoxy-2- (benzenesulfonyl) -2,3,4, 5-tetrahydro-1H-pyrido [4,3-b ] indole;
s3, adding sodium hydride into N2Adding into DMF under atmosphere, cooling to 15 deg.C, slowly adding 8-methoxy-2- (benzenesulfonyl) -2,3,4, 5-tetrahydro-1H-pyrido [4,3-b ] obtained in step S2]Indole, transAfter 0.5H, dripping benzene sulfonyl chloride, controlling the reaction temperature, and reacting for 12H to obtain 8-methoxy-2- (phenylsulfinyl) -5- (phenylsulfonyl) -2,3,4, 5-tetrahydro-1H-pyrido [4,3-b ]]Indole;
s4, adding the 8-methoxy-2- (phenylsulfinyl) -5- (phenylsulfonyl) -2,3,4, 5-tetrahydro-1H-pyrido [4,3-b ] indole obtained in the step S3 into 1, 4-dioxane, adding selenium dioxide, controlling the reaction temperature to be 100 ℃ and 110 ℃, and reacting for 3d to obtain 8-methoxy-5- (phenylsulfonyl) -5H-pyrido [4,3-b ] indole;
s5, adding the 8-methoxy-5- (benzenesulfonyl) -5H-pyrido [4,3-b ] indole obtained in the step S4 into a mixed solvent of tetrahydrofuran and water, then adding an inorganic base, controlling the reaction temperature to be 90-100 ℃, and reacting for 12H to obtain the 8-methoxy-5H-pyrido [4,3-b ] indole.
2. The method of synthesis of claim 1, wherein: the reaction temperature in the step S2 is 20-30 ℃.
3. The method of synthesis of claim 1, wherein: the inorganic base is one of sodium carbonate, potassium carbonate, sodium bicarbonate and potassium bicarbonate.
4. The method of synthesis of claim 1, wherein: the reaction temperature in the step S3 is 20-30 ℃.
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