Tag: M.W=200-300

Electric Literature of 99548-54-6,Some common heterocyclic compound, 99548-54-6, name is Methyl 3-bromo-2-methylbenzoate, molecular formula is C9H9BrO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Example 110 methyl { (3S) -6- [ (3-bromo-2-methylbenzyl) amino] -2, 3-dihydro-l- benzofuran-3-yl } acetate; [0990][0991]Methyl 3-bromo-2-methylbenzoate (2.29 g, 10.0 mmol) was dissolved in tetrahydrofuran (50 mL) , under ice-cooling, lithium aluminum hydride (0.285 g, 7.50 mmol) was added by small portions, and the mixture was stirred under a nitrogen atmosphere for 2 hr. Sodium sulfate 10 hydrate (2.42 g, 7.50 mmol) was added to the reaction mixture, and the mixture was stirred at room temperature for 2 hr. Insoluble material was filtered off through celite, and the filtrate was concentrated under reduced pressure. The obtained solid was recrystallized from heptane-ethyl acetate to give 3-bromo-2-methylbenzyl alcohol (1.76 g, yield 88%) as colorless crystals. This product (0.943 g, 4.69 mmol) was dissolved in acetonitrile (25 mL) , a Dess-Martin reagent (2.39 g, 5.63 mmol) was added by small portions under ice-cooling, and the mixture was stirred at room temperature for 0.5 hr. The reaction mixture was treated with saturated aqueous sodium hydrogen carbonate and aqueous sodium thiosulfate solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. A solution of the obtained colorless oil, methyl [ (3S) -6-amino-2, 3-dihydro-l- benzofuran-3-yl] acetate (0.972 g, 4.69 mmol) and acetic acid(0.537 mL, 9.38 mmol) in acetonitrile (25 mL) was stirred under a nitrogen atmosphere at room temperature for 0.5 hr. Sodium triacetoxyborohydride (1.99 g, 9.38 mmol) was added to the reaction mixture, and the mixture was further stirred for 12 hr. The reaction mixture was treated with water and saturated aqueous ammonium chloride solution, and extracted with ethyl acetate. The extract was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate rhexane = 5:95-40:60) to give the title compound (1.59 g, yield 87%, 2 steps) as a colorless oil.1H NMR (300 MHz, CDCl3) delta 2.42 (3H, s) , 2.48-2.59 (IH, m) , 2.68-2.78 (IH, m) , 3.68-3.83 (4H, m) , 3.89 (IH, br s) , 4.18- 4.30 (3H, m) , 4.71 (IH, t, J = 9.1 Hz), 6.07-6.16 (2H, m) , 6.93 (IH, d, J = 8.0 Hz), 7.01 (IH, t, J = 7.9 Hz), 7.23-7.30(IH, m) , 7.49 (IH, dd, J = 7.9, 1.1 Hz). MS m/z 390 (M + H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 3-bromo-2-methylbenzoate, its application will become more common.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; NEGORO, Nobuyuki; TERAO, Yoshito; MIKAMI, Satoshi; YUKAWA, Tomoya; WO2010/143733; (2010); A1;,
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Reference of 1215205-50-7, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 1215205-50-7 as follows.

Step 4: 1-[4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-cyclopropanecarboxylic acid ethyl ester 1-(4-Bromo-phenyl)-cyclopropanecarboxylic acid ethyl ester (3 g, 13.mmol), bis(pinacolato)diboron (3.37 g, 16.1 mmol), and potassium acetate (2.8 g, 29.0 mmol) were combined in 1,4-dioxane (30 mL) under N2. The solution was purged with N2 for 10 minutes, then (1,1′-bis(diphenylphosphino)ferrocene)-dichloropalladium(II) (0.50 g, 0.65 mmol) was added and the reaction was heated to 80 C. for 2 hours. After aqueous workup, the crude material was purified by silica gel chromatography (0-30% EtOAc in hexanes) to give the title compound.

According to the analysis of related databases, 1215205-50-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Amira Phamaceuticals, Inc.; US2011/82181; (2011); A1;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 126541-82-0, name is Methyl 3-amino-4-(trifluoromethyl)benzoate, A new synthetic method of this compound is introduced below., Formula: C9H8F3NO2

To a mixture of methyl 3-amino-4-(trifluoromethyl)benzoate (15 g, 0.073 mol) and aqueous HC1 solution (i2 M, 24 mL) in H20 (i00 mL) at 0 C was added dropwise a solution of NaNO2 (5.5 g, 0.080 mol) in H20 (30 mL). The reaction was stined at 0 C for 30 mm and then added dropwise to a sluny of CuCN (7.1 g, 0.080 mol) and KCN (8.4 g, 0.i3 mol) in H20 (200 mL), while maintaining the internal temperature between 5-1 0 C. After the addition was complete, the reaction was heated at 80 C for 1 h. The mixture was cooled and the solution was extracted with EtOAc (200 mL x 4). The combined organic layers were dried over anhydrous Na2504 and concentrated. The residue was purified by column chromatography on silica gel (2% EtOAc in PE) to afford the title compound. MS: m/z = 230.0 (M + 1). ?H NMR (400 MHz, CDC13)oe 8.46-8.53 (m, 1H), 8.33-8.42 (m, 1H), 7.87-7.95 (m, 1H), 4.01 (s, 3H).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; MERCK SHARP & DOHME CORP.; STUMP, Craig A.; CHEN, Yi Heng; LIU, Ping; MENG, Dongfang; WU, Jane; LI, Chun Sing; QI, Zhiqi; (163 pag.)WO2016/161572; (2016); A1;,
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Some common heterocyclic compound, 935273-86-2, name is Benzyl 3,3-difluorocyclobutanecarboxylate, molecular formula is C12H12F2O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Recommanded Product: 935273-86-2

Benzyl 3,3-difluorocyclobutanecarboxylate (2-C) (0.84 g, 3.72 mmol) was dissolved in ethanol (40 ml), and approximately 20 mg of palladium on activated carbon was added. The mixture was stirred at room temperature under hydrogen atmosphere for 12 hours, and then filtered through a pad of Celite. The filtrates were concentrated and dried in vacuo to give 2-D. lH NMR (500 MHz, CDCI3): delta2.86-2.93 (4H, m), 3.02-3.04 (IH, m) ppm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 935273-86-2, its application will become more common.

Reference:
Patent; MERCK & CO., INC.; WO2007/47625; (2007); A2;,
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Application of 56441-97-5, A common heterocyclic compound, 56441-97-5, name is Methyl 4-(benzyloxy)-3-methoxybenzoate, molecular formula is C16H16O4, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Commercially available methyl 4-hydroxy-3-methoxy-benzoate 1 was converted in 5 steps to 4-(3-fluoroanilino)-6-methoxy-7-benzyloxy-quinazolme 15 (35% overall yield).[17,18] The only significant modification involved an improved workup of the nickel chloride hexahydrate-sodium borohydride reduction of the nitro intermediate. Debenzylation with trifluoroacetic acid to give the 7-hydroxy intermediate 16, followed by alkylation with propargyl bromide in acetonitrile, gave 13 in a 65% yield for 2 steps. This method involved an additional step, and the overall yield was greater. In addition, the final 7-hydroxy intermediate 16 could be used to generate other products [19].

The synthetic route of 56441-97-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NORTHEASTERN UNIVERSITY; HANSON, Robert, N.; WO2010/85747; (2010); A1;,
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Electric Literature of 69812-51-7, These common heterocyclic compound, 69812-51-7, name is Methyl 4-chlorosulfonylbenzoate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: To a solution of compounds 1a-1e or methyl 4-aminobenzoate (1.0 mmol) in pyridine (3.0 mL), the corresponding sulfonyl chloride (1.3 mmol) in pyridine (3.0 mL)were added dropwise under nitrogen atmosphere at 0 C, then the reaction mixture was stirred at room temperature overnight. The reaction was then acidified to pH=1 with 4NHCl(aq) and the resulting solid was collected by filtration. The crude product was purified by flash column chromatography (ethyl acetate-petroleum ether = 1:2) to give the title compounds 2a-2i.

Statistics shows that Methyl 4-chlorosulfonylbenzoate is playing an increasingly important role. we look forward to future research findings about 69812-51-7.

Reference:
Article; Zhang, Jiankang; Shen, Luqing; Wang, Jincheng; Luo, Peihua; Hu, Yongzhou; Medicinal Chemistry; vol. 10; 1; (2014); p. 38 – 45;,
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Related Products of 14273-90-6,Some common heterocyclic compound, 14273-90-6, name is Methyl 6-bromohexanoate, molecular formula is C7H13BrO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a solution of 4-piperidone (0.125 g, 1.26 mmol) in anhydrous DMF (2 ml), K2CO3 (0.2 g, 1.51 mmol), 21 (0.52 g, 2.48 mmol) and KI (0.015 g, 0.090 mmol) were added to the mixture. The reaction mixture was stirred at r.t. for 36 hours under N2. The reaction mixture was filtered off and filtrate was concentrated and dried under vacuum providing a white solid (0.29 g, 98%) of compound 22. Product was used without further purification to the next step. (0431) 1H NMR (400 MHz, Chloroform-d) delta: 3.64 (d, J=2.0 Hz, 3H), 3.38 (t, J=6.7 Hz, 2H), 2.70 (t, J=6.2 Hz, 2H), 2.42 (t, J=6.8 Hz, 4H), 2.30 (t, J=7.4 Hz, 4H), 1.85 (p, J=7.0 Hz, 2H), 1.70-1.56 (m, 4H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 6-bromohexanoate, its application will become more common.

Reference:
Patent; Ecole Polytechnique Federale de Lausanne (EPFL); Sinisi, Riccardo; Morales Morales, Alma Rosa; Dubikovskaya, Elena A.; Singh, Rajendra; (103 pag.)US2018/79906; (2018); A1;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 56441-97-5, name is Methyl 4-(benzyloxy)-3-methoxybenzoate, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 56441-97-5

E) 4-Benzyloxy-3-methoxy benzoic acid; A solution of sodium hydroxide (2.0 g) in methanol (50 ml) was added to a solution of 4-benzyloxy-3-methoxy benzoic acid methyl ester (4.64 g) in methanol (50 ml) and refluxed for 4 hrs. After removal of methanol under reduced pressure the residue was dissolved in water (150 ml) and washed with ethyl acetate (2 x 50 ml). The aqueous layer was acidified with 2N hydrochloric acid to pH 2. The precipitated product was collected by filtration which on drying under vacuum provided 4.17 g of 4-benzyloxy- 3-methoxy benzoic acid. (Yield = 74%) ‘H NMR CDCl3 7.7 (1H, d, J = 8Hz) 7.63 (1H, s) 7.3-7.5 (5H, m) 6.92 (1H, d, J 8Hz) 5.25 (2H, s) 3.98 (3H, s)

According to the analysis of related databases, 56441-97-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PROTEOTECH, INC.; WO2005/113489; (2005); A1;,
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Reference of 25542-62-5, These common heterocyclic compound, 25542-62-5, name is Ethyl 6-bromohexanoate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Example-2 Preparation of N-(5-Ethoxycarbonylpentyl)-3-(1-naphthoyl)-1H-indole 2 To a suspension of sodium hydride (1.1 g, 30 mmol, 60% in mineral oil) in DMF (100 ml) under nitrogen was added solid 3-(1-naphthoyl)-1H-indole 1 (5.43 g, 20 mmol). After stirring at room temperature for 1 h, a solution of ethyl 6-bromohexanoate (6.6 g, 30 mmol) in DMF (10 ml) was added slowly with stirring over a period of 15 min and the mixture was then heated at 60 C. for 3 h. The solvent was removed under high vacuum and the crude product was suspended in water (150 ml) and extracted by ethyl acetate (2*150 ml). The combined ethyl acetate phases were washed by water (1*100 ml), brine (1*100 ml), dried over sodium sulphate filtered and concentrated to dryness. The crude product obtained was purified by chromatography on silica gel using hexane/ethyl acetate (8/2) to give the title compound 2 as an oil which became solid in the cold (7.1 g, 86%).

The synthetic route of 25542-62-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RANDOX LABORATORIES LIMITED; US2012/208213; (2012); A1;,
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Adding a certain compound to certain chemical reactions, such as: 1186-73-8, name is Trimethyl methanetricarboxylate, belongs to esters-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 1186-73-8, Recommanded Product: Trimethyl methanetricarboxylate

N-benzyl-3-isopropyl-7-methoxy-6-(3-methoxypropoxy)tetralin-1-imine (1 g, 2.53 mmol) and trimethyl methanetricarboxylate (1.44 g, 7.6 mmol) were dissolved in diglyme (10 mL). The reaction mixture was stirred at 180 C in a microwave reactor for 30 minutes. Ethyl acetate (20 mL), followed by H2O (30 mL) were added to the reaction mixture. The separated organic layer was washed with H2O (2 x 20 mL), saturated aqueous brine solution (2 x 20 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude residue was purified by normal phase SiO2; chromatography (0 to 70 % EtO Ac/hexanes) to give methyl 1-benzyl-4-hydroxy-5-isopropyl-9-methoxy-8-(3-methoxypropoxy)-2-oxo-1,2,5,6-tetrahydrobenzo[h]quinoline-3-carboxylate as a yellow oil (560 mg, 42% yield, m/z: 522 [M+H] observed).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Trimethyl methanetricarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; ARBUTUS BIOPHARMA, INC.; CHEN, Shuai; DORSEY, Bruce D.; FAN, Yi; GOTCHEV, Dimitar B.; QUINTERO, Jorge; (252 pag.)WO2019/177937; (2019); A1;,
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