Tag: M.W=100-200

Synthetic Route of 924-99-2,Some common heterocyclic compound, 924-99-2, name is Ethyl 3-(dimethylamino)acrylate, molecular formula is C7H13NO2, 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: The substituted benzoyl chloride (18.1 mmol), 3-(N,N-dimethylamino)acrylic acid ethyl ester (18.1 mmol), triethylamine (27.1 mmol) was dissolved in 30 mL of toluene, stirred at 90 C for 4 h, concentrated and column chromatographed to give Intermediate 1. ethyl 2-(2,4-difluorobenzoyl)-3-(dimethylamino)acrylate (R2=H): yield 65%

The synthetic route of 924-99-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Fudan University; Chen, Fen Er; He, Qiuqin; Mao, Tianqi; Wan, Zhengyong; (17 pag.)CN103965163; (2016); B;,
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Adding a certain compound to certain chemical reactions, such as: 35613-44-6, name is Methyl 2-(2-aminophenyl)acetate, 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 35613-44-6, name: Methyl 2-(2-aminophenyl)acetate

Preparation of tert-butyl 4-(2-oxoindolin- 1 -yl)piperidine- 1 -carboxylate (Compound 11-4) [00270j A mixture of methyl 2-(2-aminophenyl)acetate (Compound 11-3, 3.30 g, 20 mmol), tert-butyl 4-oxopiperidine-1-carboxylate (4.38 g, 22 mmol), acetic acid (HOAc, 600 mg, 10 mmol) in dichloromethane (DCM, 80 mL) was stirred at room temperature for 2 h, then sodium triacetoxyborohydride (NaBH(OAc)3, 6.36 g, 30 mmol) was added in portions and heated to 40C, stirred overnight. The reaction mixture was cooled to room temperature and diluted with dichloromethane (DCM, 200 mL), washed with water (200 mL x 2) and sodium bicarbonate (sat. aq., 200 mL x 2), dried over anhydrous sodium sulfate, concentrated to give the crude product, purified by flash colunm chromatography on silica gel (ethyl acetate petroleum ether, 1 20-1 15-1 10 v v) to give the desired product tert-butyl 4-(2-oxoindolin- 1 -yl)piperidine- 1- carboxylate (Compound 11-4, 2.65 g, yield: 42%) as a pale yellow solid. MS (ESI):mlz: 261[M+H-56]. ?H NMR (400 MHz, CDC13) oe: 7.24 (m, 2H), 7.01 (m, 2H), 4.41 (m, 1H), 4.28 (br s, 2H), 3.53 (s, 2H), 2.83 (br s, 2H), 2.32 (m, 2H), 1.70 (m, 2H), 1.50 (s, 9H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2-(2-aminophenyl)acetate, and friends who are interested can also refer to it.

Reference:
Patent; FANG, Qun, Kevin; SPEAR, Kerry, L.; CAMPBELL, Una; WO2014/106238; (2014); A1;,
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These common heterocyclic compound, 7270-63-5, name is 5-Diazo-2,2-dimethyl-1,3-dioxane-4,6-dione, 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. Computed Properties of C6H6N2O4

General procedure: To a solution of diazo compound 1 (0.5 mmol) and alkynes (1.1 mmol) in toluene (2 mL) was added rhodium(II) pivalate (0.01 mmol). The reaction mixture was stirred at 60C for 0.5-5 h. The solvent was evaporated in rotary evaporator under reduced pressure to give the residue. The residue was purified by flash column chromatography on silica gel to give the product. 4.2.1. 2,4-Diphenyl-6H-furo[2,3-b]pyran-6-one (4). Reaction of 1 (85 mg, 0.5 mmol) and phenylacetylene (112 mg, 1.1 mmol) under Rh2(OPiv)4 (6 mg, 0.01 mmol) afforded 4 (86 mg, 60%) as a solid: mp 88-90 C; 1H NMR (300 MHz, CDCl3) delta 7.64-7.62 (4H, m), 7.55-7.52 (3H, m), 7.39 (2H, t, J=7.5 Hz), 7.30 (1H, d, J=7.5 Hz), 6.87 (1H, s), 6.21 (1H, s); 13C NMR (75 MHz, CDCl3) delta 159.6, 159.1, 154.0, 148.7, 135.3, 131.0, 129.4, 129.1, 128.5, 127.7, 123.7, 105.0, 101.0, 99.9; IR (KBr) 1724, 1607, 1526, 1379, 1295, 1195, 826, 761, 687 cm-1; HRMS m/z (M+) calcd for C19H12O3: 288.0786. Foud: 288.0790.

The synthetic route of 5-Diazo-2,2-dimethyl-1,3-dioxane-4,6-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Somai Magar, Krishna Bahadur; Lee, Yong Rok; Kim, Sung Hong; Tetrahedron; vol. 69; 44; (2013); p. 9294 – 9302;,
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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. 17205-02-6, name is Ethyl 3-hydroxycyclobutanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 17205-02-6

3-hydroxy-cyclobutane-carboxylic acid ethyl (800 mg)In tetrahydrofuran (25mL) solution,Synthesized in Reference Example 2-53 (1) 2-chloro-4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenol (4.24 g),Triphenylphosphine (5.68g),Toluene solution of diethyl azodicarboxylate (2.2M, 9.84mL) was added,It was stirred at room temperature for 13 hours. The temperature was raised to 60 , and the mixture was stirred for 7 hours at the same temperature.The solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane: ethyl acetate = 100: 0 ? 70: 30) in the purified twice, to give the title compound (2.22g) as a colorless solid .

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 17205-02-6.

Reference:
Patent; TAISHO PHARMACEUTICAL COMPANY LIMITED; NISSAN CHEMICAL INDUSTRIES LIMITED; KURODA, SHOICHI; USHIKI, YASUNOBU; KAWAGUCHI, TAKANORI; FUSEGI, KEIKO; BOHNO, MASAHIRO; IMAI, YUDAI; UNEUCHI, FUMITO; IWAKIRI, KANAKO; TANAKA, HIROAKI; BOHNO, AYAKO; CHONAN, TOMOMICHI; ITOH, SHIN; OTA, HIROFUMI; ISHIYAMA, SEISHI; OKADA, TAKUYA; SASAKO, SHIGETADA; MONMA, SOUICHI; NIWA, MARIE; OKADA, TAKUMI; (289 pag.)JP2015/231988; (2015); A;,
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Synthetic Route of 14062-24-9, 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. 14062-24-9, name is Ethyl 4-chlorophenylacetate, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 2 2-(alpha-ethoxycarbonyl-4-chlorobenzylidene)-1-methylperhydroazepine Add (drop by drop at 90 in a stream of nitrogen to let the alcohol escape) a solution of 4.6 g of sodium in 100 ml of ethyl alcohol to a mixture of 53.2 g of the title compound of Example 1 and 29.8 g of ethyl 4-chlorophenylacetate. Stir it for a further 4 hours at 90 and then cool it to ambient temperature. Mix the cooled reaction mixture with 100 ml of water and 100 ml of diethyl ether, collect the organic phase and dry the latter over sodium sulfate. Concentrate the dried organic phase and then distil off any excess ethyl 4-chlorophenylacetate under a high vacuum to obtain a crude yield [15.5 g (34% of theory)] of the title compound as yellow oil.

The chemical industry reduces the impact on the environment during synthesis Ethyl 4-chlorophenylacetate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Byk Gulden Lomberg Chemische Fabrik GmbH; US4221788; (1980); A;,
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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. 61367-07-5, name is Methyl trans-4-aminocyclohexanecarboxylate hydrochloride, A new synthetic method of this compound is introduced below., category: esters-buliding-blocks

(1) Methyl trans-4-aminocyclohexanecarboxylate hydrochloride (10 g) obtained in Reference Example 2(1), 1,4-diiodobutane (19.2 g) and sodium carbonate (16.4 g) are suspended in a mixture of tetrahydrofuran (300 ml) and N,N-dimethyl acetamide (60 ml), and the mixture is stirred at 70C for 20 hours. The reaction solution is concentrated under reduced pressure. The residue is dissolved in ethyl acetate/water and the organic layer is separated. The organic layer is washed with water and saturated brine, dried over sodium sulfate and evaporated to remove the solvent under reduced pressure. The resulting residue is purified by NH-silica gel column chromatography (eluent: ethyl acetate/hexane = 1/5) to give methyl trans-4-pyrrolidin-1-ylcyclohexanecarboxylate (10.9 g). APCI-MS M/Z:212[M+H]+.

The synthetic route of 61367-07-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TANABE SEIYAKU CO., LTD.; EP1582521; (2005); A1;,
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Application of 15568-85-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 15568-85-1 name is 5-(Methoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

1 eq of 3-bromo-2-methoxy-4-aminopyridine was dissolved in isopropanol, then 2 eq of compound 49 was added thereto. After heating to 110 C., the mixture was allowed to react for 1 h with stirring, and then a large amount of solid was precipitated. 2 h later, the solid was cooled to room temperature, washed with isopropanol and ether to give the product compound 57, yield 92%; The compound obtained above was suspended in diphenyl ether at 10 ml/g, and the mixture was heated to 220 C. and allowed to react for 1 h with stirring, and then a large amount of solid was precipitated, which was cooled to room temperature, washed with a large amount of petroleum ether and filtered to give the compound 58, yield 96%. The above solid was dissolved in methanol, and 2 eq of ammonium formate was added therein followed by the addition of 10 wt % of 10% Pd/C. The mixture was allowed to react with stirring at 60 C. and the reaction was monitored by TLC. After the reaction was completed, the resultant was cooled and filtered, the filtrate was concentrated and then extracted with EA, washed with saturated NaCl, dried over anhydrous Na2SO4 and concentrated under reduced pressure to give the compound 59. 1H NMR (400 MHz, DMSO) delta 8.89 (s, 1H), 8.46 (s, 1H), 7.87 (d, J=7.6 Hz, 1H), 6.75 (s, 1H), 5.97 (d, J=7.6 Hz, 1H), 3.91 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-(Methoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione, and friends who are interested can also refer to it.

Reference:
Patent; SHANGHAI INSTITUTE OF MATERIA MEDICA, CHINESE ACADEMY OF SCIENCES; LONG, Yaqiu; GENG, Meiyu; XU, Zhongliang; AI, Jing; (100 pag.)US2018/244667; (2018); A1;,
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These common heterocyclic compound, 73792-08-2, name is Methyl 4-amino-2-fluorobenzoate, 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. Formula: C8H8FNO2

General procedure: The obtained compound was dissolved in methylene chloride, and the solution was cooled to -10 C. Then, a methylene chloride solution (200 ml) of methyl 4-amino-2-fluorobenzoate (16.9 g, 100 mmol) and pyridine (10 ml) was added thereto, followed by stirring at room temperature for 2 hours. The reaction solution was washed with 0.1 N hydrochloric acid (200 ml×2). Then, the organic layers were combined and dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=2:1 to 1:1) to obtain the title compound (12.4 g, 40%). [0715] MS (ESI) m/z 311 (M+H)+

The synthetic route of Methyl 4-amino-2-fluorobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AJINOMOTO CO., LTD.; Ueno, Hirokazu; Yamamoto, Takashi; Takashita, Ryuta; Yokoyama, Ryohei; Sugiura, Toshihiko; Kageyama, Shunsuke; Ando, Ayatoshi; Eda, Hiroyuki; Eviryanti, Agung; Miyazawa, Tomoko; Kirihara, Aya; Tanabe, Itsuya; Nakamura, Tarou; Noguchi, Misato; Shuto, Manami; Sugiki, Masayuki; Dohi, Mizuki; US2015/51395; (2015); A1;,
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Some common heterocyclic compound, 454-31-9, name is Ethyl 2,2-difluoroacetate, molecular formula is C4H6F2O2, 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. Quality Control of Ethyl 2,2-difluoroacetate

Step 1: Preparation of 1-ethoxy-2,2-difluoroethanol To a solution of ethyl 2,2-difluoroacetate (200 g, 1.59 mol) in tert-butyl methyl ether (1200 mL) was added LiAlH4 (33 g, 0.78 mol) portionwise at 78 C. under a nitrogen atmosphere. Once the addition was complete, the reaction mixture was continually stirred for 6 hrs at 78 C. EtOH (75 mL, 98%) was added dropwise to quench the reaction at 78 C., and the resulting mixture was allowed to warm to rt. The mixture was poured into ice/water, and concentrated H2SO4 (100 mL) was added carefully with stirring. The mixture was extracted with tert-butyl methyl ether (two*1 L) and the combined organic layers were washed with water, dried over Na2SO4, and concentrated to afford crude material that was submitted to distillation under reduced pressure. The fraction was collected at 45-55 C./-0.1 MPa to afford the title compound (75 g, 37% yield) as a colorless liquid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 454-31-9, its application will become more common.

Reference:
Patent; PFIZER INC.; Cheng, Hengmiao; Johnson, JR., Theodore Otto; Kath, John Charles; Liu, Kevin Kun-Chin; Lunney, Elizabeth Ann; Nagata, Asako; Nair, Sajiv Krishnan; Planken, Simon Paul; Sutton, Scott Channing; US2013/79324; (2013); 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. 711-01-3, name is Methyl adamantane-1-carboxylate, A new synthetic method of this compound is introduced below., category: esters-buliding-blocks

Under a nitrogen atmosphere, 30.5 g (4.4 mol) of lithium metal (Li) was added to 2 L of tetrahydrofuran (THF) and stirred for 1 hour.Among these, 300 g (2.0 mol) of 2-adamantanone and 258.0 g (3.3 mol) of 2-chloropropane were added to THF 1000.The solution dissolved in mL,It dripped over 30 minutes, cooling so that 20 degrees C or less might be maintained.After completion of the addition, stir at 90 ° C. for 90 minutes,A THF solution of lithium 2-isopropyl-2-adamantyl alcoholate was obtained.362.0 g of methacrylic anhydride in this THF solution(2.4 mol) was dripped over 15 minutes, cooling so that 20 degrees C or less might be maintained. After completion of the dropwise addition, the mixture was stirred at 20 ° C. for 60 minutes to synthesize 2-isopropyl-2-adamantyl methacrylate.After completion of the reaction, 4 L of toluene was added, and further, 2000 mL of 0.2 N aqueous NaOH solution was added, and the mixture was stirred at 20 ° C. for 60 minutes.After removing the aqueous phase, washing was performed twice with 2 L of pure water.By distilling off the solvent from the organic phase,517.0 g (crude yield 99percent, GC purity 84.9percent) of crude 2-isopropyl-2-adamantyl methacrylate was obtained. continue,0.7 g of p-methoxyphenol as a polymerization inhibitor is added to the obtained crude 2-isopropyl-2-adamantyl methacrylate,0.1 kPa, 10 while bubbling dry air from the capillarySimple distillation at 0 to 120 ° C,369.0 g of distilled 2-isopropyl-2-adamantyl methacrylate (GC purity 88.2percent, referred to as ?distillate B?) was obtained.

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; Osaka Organic Chemical Industry Co., Ltd.; Kojima, Akio; Kono, Naoya; Uenoyama, Yoshitaka; (19 pag.)JP2019/34959; (2019); A;,
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