Month: June 2021

Synthetic Route of 217314-47-1, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 217314-47-1, name is Methyl 3-amino-5-methoxybenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(i) Methyl 3-((4-((4-((tert-butoxycarbonvnamino)naphthalen-1-yl)oxy)pyridin-2-yl)amino)-5-methoxybenzoateA flask charged with tert-butyl (4-((2-chloropyridin-4-yl)oxy)naphthalen-1-yl)carbamate (see Example 2(ii) above; 20.1 g, 54.2 mmol), methyl 3-amino-5-methoxybenzoate (10.80 g, 59.6 mmol), BrettPhos G1 Precatalyst (550 mg, 0.689 mmol) and K2C03(14.98 g, 108 mmol) in anhydrous tBuOH (300 ml.) was back filled with nitrogen (x3) and then placed on a heating block (preheated to 90C). The suspension was degassed with nitrogen, stirred for 8 h and then cooled to rt and stirred for 8 h. Reaction mixture was warmed to 50C then cooled to rt and diluted with DCM (1 L), the suspension was filtered through Celite and the solvent evaporated. The brown oil was sonicated with diethyl ether (500 ml.) and the solid filtered under suction, washing with further diethylether, to afford the sub-title compound (21.55 g) as a beige solid. 1H NMR (400 MHz, DMSO-d6) delta 9.37 (s, 1 H), 9.19 (s, 1 H), 8.15 (s, 1 H), 8.13 (s, 1 H), 7.85 (dd, 1 H), 7.76 (dd, 1 H), 7.69 (dd, 1 H), 7.66-7.54 (m, 3H), 7.37 (d, 1 H), 6.96 (dd, 1 H), 6.62 (dd, 1 H), 6.09 (d, 1 H), 3.82 (s, 3H), 3.75 (s, 3H), 1.53 (s, 9H). (90% purity). LCMS m/z 516 (M+H)+(ES+); 514 (M-H)”(ES”)

The synthetic route of Methyl 3-amino-5-methoxybenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RESPIVERT LIMITED; TOPIVERT PHARMA LIMITED; FYFE, Matthew Colin Thor; THOM, Stephen Malcolm; BAKER, Thomas Matthew; HARBOTTLE, Gareth William; HASIMBEGOVIC, Vedran; RIGBY, Aaron; WO2015/92423; (2015); A1;,
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Electric Literature of 54535-22-7,Some common heterocyclic compound, 54535-22-7, name is Diethyl 2-((phenylamino)methylene)malonate, molecular formula is C14H17NO4, 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: A diphenyl ether solution of 2e-k (4 mmol) containingcatalytic 2-chlorobenzoic acid was heated by microwaveirradiation (250 C) for 1-2 h. After cooling, the reactionmixture was filtered and the precipitate 3e-k was washedwith n-hexane and water. Ethyl 4-oxo-1,4-dihydroquinoline-3-carboxylate (3e) Starting from 2e (5 g); Yield (cream powder): 3 g (75 %); m.p. 261-262 C; IR (KBr) numax 1400-1600 (aromatic), 1695(carbonyl), 3150 (N-H) cm-1; LC-MS (ESI) m/z 218.1 (M+H+), 240.1 (M+Na+); Calcd. for C12H11NO3: C, 66.35; H,5.10; N, 6.45. Found: 66.47; H, 5.22; N, 6.27.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Diethyl 2-((phenylamino)methylene)malonate, its application will become more common.

Reference:
Article; Hajimahdi; Zabihollahi; Aghasadeghi; Ashtiani, S. Hosseini; Zarghi; Medicinal Chemistry Research; vol. 25; 9; (2016); p. 1861 – 1876;,
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Synthetic Route of 13831-03-3, A common heterocyclic compound, 13831-03-3, name is tert-Butyl propiolate, molecular formula is C7H10O2, 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: Preparation of Copper Acetylides; Procedure 1To a solution of CuI (3.8 g, 20.0 mmol) in a mixture of NH4OH(28% NH3 solution, 50 mL) and EtOH (30 mL) was added the alkyne1 (10.0 mmol) dropwise. The deep blue reaction mixture wasstirred overnight at r.t. under argon and the yellow precipitate wascollected by filtration and successively washed with NH4OH (10%NH3 solution, 3 × 50 mL), H2O (3 × 50 mL), EtOH (3 × 50 mL), andEt2O (3 × 50 mL). The bright yellow solid was then dried under highvacuum overnight to afford the desired polymeric copper acetylide2, which was used without further purification.

The synthetic route of 13831-03-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Theunissen, Cedric; Lecomte, Morgan; Jouvin, Kevin; Laouiti, Anouar; Guissart, Celine; Heimburger, Jeremy; Loire, Estelle; Evano, Gwilherm; Synthesis; vol. 46; 9; (2014); p. 1157 – 1166;,
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Application of 10601-80-6, 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 10601-80-6 as follows.

General procedure: A mixture of Yb(OTf)3 (2.5 mol%), amine (1.0 eq.), ethyl 3,3-diethoxypropionate (2.5 eq.) and aldehyde (1.1 eq.) in 1,4-dioxane (1.5 mL / 1 eq.) was stirred at 90 C for 6-17 h. After the reaction, the resulting mixture was washed with PBS buffer solution (25 mL) and extracted with CH2Cl2 (15 mL×3). The organic layer was dried over MgSO4. Removal of the solvent in vacuo, followed by chromatography on silica gel column (AcOEt/Hexane or CHCl3/MeOH), afforded dihydropyridine 4.

According to the analysis of related databases, 10601-80-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Sueki, Shunsuke; Takei, Ryo; Abe, Junya; Shimizu, Isao; Tetrahedron Letters; vol. 52; 34; (2011); p. 4473 – 4477;,
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Application of 349-43-9,Some common heterocyclic compound, 349-43-9, name is Ethyl 2-fluoropropionate, molecular formula is C5H9FO2, 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.

Syntheses of the intermediate sulfinamide esters A3.3 and A3.4A3.3 A3.4 In a dry apparatus under an inert atmosphere a solution of diisopropylamine (3.35 g, 101 mmol) in tetrahydrofuran (25 ml) was treated with n-butyl lithium (1.6M in hexane, 20.7 ml). The solution was stirred at -7 °C for 40 minutes. Thereafter, the solution was cooled to -75 °C and a solution of ethyl 2-fluoropropanoate (3.98 g, 33.2 mmol) in tetrahydrofuran (5 ml) was added dropwise. After 40 minutes a solution of chlorotitanium triisopropoxide (8.64 g, 33.2 mmol) in tetrahydrofuran (15 ml) was slowly added dropwise. After 40 minutes at -72 °C to the orange colored solution was added dropwise a solution of (R)-2-methyl-propane-2-sulfinic acid [l-(2-fluorophenyl)-(E)-ethylidene] -amide (intermediate A2.1) (4.0 g, 16.6 mmol) in tetrahydrofuran (5 ml). Stirring was continued at -72 °C for 4 hours, then the reaction mixture was kept at -20 °C for 17 hours. For the workup, the reaction mixture was quenched with an aqueous solution of ammonium chloride (13percent, 100 ml). The precipitate formed was diluted with water and the resulting mixture extracted three times with ethyl acetate. The organic layers were washed with brine, then combined, dried and evaporated at reduced pressure. Purification of the crude product by chromatography on silica gel using a 5:2-mixture auf heptane and ethyl acetate as the eluent yielded a l :2-mixture of the (2S,3R)-2-fluoro-3-(2-fluoro-phenyl)-2-methyl-3- ((R)-2-methyl-propane-2-sulfinylamino)-butyric acid ethyl ester (A3.3) and (2R,3R)-2-Fluoro-3- (2-fluoro-phenyl)-2-methyl-3-((R)-2-methyl-propane-2-sulfinylamino)-butyric acid ethyl ester (A3.4) (4.43 g, 74percent) as a light yellow oil. MS (ISP): m/z = 362.2 [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 Ethyl 2-fluoropropionate, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; SIENA BIOTECH S.P.A; HILPERT, Hans; WOSTL, Wolfgang; WO2012/139993; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 3697-68-5, name is Ethyl 1-(hydroxymethyl)cyclopropanecarboxylate, molecular formula is C7H12O3, 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: C7H12O3

[0373] To a stirring ice-cooling solution of compound 72(200 mg, 1.39 mmol) and triethylamine (280 mg, 2.77 mmol)in DCM (10 ml), was added methanesulfonyl chloride (190mg, 1.66 mmol, dissolve in 1 ml DCM) dropwise. The reactionmixture was stirred 1 hat oo C., then diluted with DCM(20 ml), the organic phase was washed with water and brine,dried over Na2S04 , filtered and concentrated to afford crudecompound 73 (300 mg, yield 97%) as a colorless oil, useddirectly in the next step without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3697-68-5, its application will become more common.

Reference:
Patent; Gao, Daxin; Yang, Heping; Yu, Yajun; US2014/329800; (2014); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics