Author: Jessica.F

Electric Literature of 33689-29-1,Some common heterocyclic compound, 33689-29-1, name is Methyl 1-hydroxycyclopropanecarboxylate, molecular formula is C5H8O3, 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 methyl 1-hydroxycyclopropanecarboxylate (0.741 mL, 8.61 mmol) was added diisopropylcarbamic chloride (1.550 g, 9.47 mmol) and DIEA (2.256 mL, 12.92 mmol) in DCM (15 mL). The resulting solution was stirred at rt for 2 h, then diluted with DCM and the organic layer was washed with 1 N HC1,water and brine, dried (Mg504), filtered and concentrated. The residue was purified via Biotage (15% to 30% EtOAc/Hex; 25 g column) to yield Cap L-9 Step a (0.66 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 1-hydroxycyclopropanecarboxylate, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; HEWAWASAM, Piyasena; LOPEZ, Omar D.; TU, Yong; WANG, Alan Xiangdong; XU, Ningning; KADOW, John F.; MEANWELL, Nicholas A.; GUPTA, Samayamunthula Venkata Satya Arun Kumar; KUMAR, Indasi J. Gopi; PUNUGUPATI, Suresh Kumar; BELEMA, Makonen; WO2015/5901; (2015); A1;,
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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. 57381-59-6, name is Methyl 5-bromo-2-fluorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 57381-59-6

Compound 33b (24.00 g, 102.99 mmol) was dissolved in methanol (300 mL), and N,N-dimethylformamide (100 mL), triethylamine (100 mL), and [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium (12.62g, 15.45 mmol) were added successively. The reaction mixture was stirred under a carbon monoxide atmosphere (50 psi) for 16 hr at 80 C, filtered, concentrated under reduced pressure to dryness, diluted with 100 mL of water, and extracted with ethyl acetate (500 mL×2). The organic phases were combined, dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure to dryness, and purified by silica gel column chromatography (petroleum ether/ethyl acetate=100-0%) to give Compound 33c (11.00 g). 1H NMR (400 MHz, CDCl3) delta3.95(s, 3H), 3.97(s, 3H), 7.20-7.24 (m, 1H), 8.21-8.23 (m, 1H), 8.63-8.65 (m, 1H). MS-ESI calculated value [M+ H]+ 213, measured value 213.

The synthetic route of 57381-59-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chia Tai Tianqing Pharmaceutical Group Co., Ltd.; Medshine Discovery Inc.; CHEN, Bin; YAO, Yuanshan; CHEN, Yuan; LI, Ao; XU, Ran; HUANG, Zhensheng; TIAN, Dongdong; LI, Hongwei; YANG, Chengshuai; LI, Jian; CHEN, Shuhui; (69 pag.)EP3489235; (2019); A1;,
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These common heterocyclic compound, 35180-01-9, name is Chloromethyl isopropyl carbonate, 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. Application In Synthesis of Chloromethyl isopropyl carbonate

After pretreating the crude tenofovir obtained in step S02,And 16L N-methylpyrrolidone, 4.44kg of triethylamine, after stirring evenly,Start to warm to 50 C, stir, add 11.15 kg of isopropyl chloromethyl carbonate,After stirring, the reaction was completely quenched by cooling, and after cooling, 12 L of cyclohexane was added twice.Stir, centrifuge, layer, discard the upper layer of cyclohexane, and transfer the filtrate from the lower layer to the reaction vessel.Add 30 L of water and 20 L of ethyl acetate, stir for 30 minutes, and let stand for stratification.The aqueous layer was extracted once with 10 L of ethyl acetate.Add 1.0 kg of anhydrous sodium sulfate, stir dry, centrifuge,The filtrate is transferred to the transfer reactor in batches, concentrated under reduced pressure, and the concentrate is transferred to the reaction vessel.Tenofovir disoproxil give crude ester.

The synthetic route of Chloromethyl isopropyl carbonate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shandong Kexing Biological Products Co., Ltd.; Zhang Yun; Hao Zhihai; Qiu Duxian; Wang Cuicui; Cui Ning; (24 pag.)CN108586532; (2018); A;,
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Related Products of 18595-18-1,Some common heterocyclic compound, 18595-18-1, name is Methyl 3-amino-4-methylbenzoate, molecular formula is C9H11NO2, 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.

In a 500-ml three-necked flask with mechanical stirrer, 20 g (121 mmol) of 3-amino-4-methylbenzoic acid methyl ester, 17.14 g ammonium tetrafluoroborate and 217 ml water are cooled to 0 C. and then 24.6 ml concentrated hydrochloric acid is added dropwise. Then a solution of 8.35 g (121.1 mmol) of sodium nitrite in 21.7 ml water is added dropwise within 20 min and stirring is continued for 40 min at 3 C. It is filtered with suction through a frit and the filter cake is mixed with methanol (100 ml), dried and then mixed with methyl-tert.-butyl ether and dried again. After vacuum drying we obtain 26.99 g (84% of th.) of the diazonium tetrafluoroborate salt, which is used further without further purification. For the production of the corresponding indazole derivative, 26.99 g of the diazonium salt (102.2 mmol) is suspended in 500 ml dichloromethane in a 1 l round-bottom flask and 1.43 g (5.4 mmol) of 18-crown-6-ether and 22.8 g (232.1 mmol) of potassium acetate are added at RT and stirred for 3 h at RT. 100 ml water is added to the suspension, the dichloromethane phase is removed and the aqueous phase is extracted once more with dichloromethane. The combined organic phases are washed with 50 ml water and dried over sodium sulphate. Chromatography on silica gel with cyclohexane/ethyl acetate gives 17.54 g (97% of th.) of the product as a solid. LCMS (method 1): Rt=1.41 min (m/z=177 (M+H)+) 1H-NMR (400 MHz, DMSO-d6): delta=13.95 (s, 1H), 8.18 (d, 2H), 7.89 (d, 1H), 7.68 (d, 1H), 3.90 (s, 3H).

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-amino-4-methylbenzoate, its application will become more common.

Reference:
Patent; BAYER HEALTHCARE AG; US2010/105663; (2010); A1;,
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Related Products of 52727-57-8, These common heterocyclic compound, 52727-57-8, name is Methyl 2-amino-5-bromobenzoate, 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.

To a mixture of methyl 2-amino-5-bromobenzoate (2.32 g, 10.1 mmol), 4-fluorophenylboronic acid (1.70 g, 12.1 mmol, 1.20 equiv), PdCl2(amphos)2 (79.0 mg, 0.112mmol, 1.1 mol %), and tripotassium phosphate n-hydrate (3.28 g, ca. 12 mmol, ca. 1.2 equiv)were added 1,4-dioxane (40 mL) and H2O (4 mL) at room temperature and the mixture washeated at 100 C with stirring for 16 h. After cooling to room temperature, the mixture wasconcentrated under reduced pressure. The mixture was extracted with EtOAc (10 mL × 3),and the combined organic extract was washed with brine (5 mL), dried (Na2SO4), and, afterfiltration, the filtrate was concentrated under reduced pressure. The residue was purified byrecrystallization from n-hexane to give methyl 2-amino-5-(4-fluorophenyl)benzoate (2.01 g,8.20 mmol, 82.0%) as a pale yellow solid.

Statistics shows that Methyl 2-amino-5-bromobenzoate is playing an increasingly important role. we look forward to future research findings about 52727-57-8.

Reference:
Article; Nakamura, Yu; Yoshida, Suguru; Hosoya, Takamitsu; Chemistry Letters; vol. 46; 6; (2017); p. 858 – 861;,
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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. 85953-29-3, name is Methyl 2-chloro-4-fluorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C8H6ClFO2

Methyl(2-chloro-4-fluorophenyl)formate (134.8 g) obtained above was suspended in conc. sulfuric acid (50 ml). To the suspension, a mixture of conc. sulfuric acid (50 ml) and conc. nitric acid (50 ml) was added at about 30 C., and the mixture was stirred for 1 hour at this temperature. The reaction mixture was poured into ice-water, and precipitated crystals were collected and washed with water. Methyl(2-chloro-4-fluoro-5-nitrophenyl)formate (143 g) was thus obtained. M.P., 53-55 C.

The synthetic route of 85953-29-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sumitomo Chemical Company, Limited; US4670046; (1987); A;,
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Related Products of 106614-28-2, A common heterocyclic compound, 106614-28-2, name is Methyl 2,4-difluorobenzoate, molecular formula is C8H6F2O2, 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 1H methyl 2-(1H-pyrrolo[2,3-b]pyridin-5-yloxy)-4-fluorobenzoate A mixture of EXAMPLE 1G (8.5 g), methyl 2,4-difluorobenzoate (7.05 g), and K3PO4 (9.32 g) in diglyme (40 mL) at 115 C. was stirred for 24 hours. The reaction was cooled, diluted with ether (600 mL), and washed twice with water, and brine, and concentrated. The crude product was chromatographed on silica gel with 2-50% ethyl acetatehexanes.

The synthetic route of 106614-28-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tao, Zhi-Fu; Wang, Xilu; Wendt, Michael; Souers, Andrew; Judd, Andrew; Kunzer, Aaron; Sullivan, Gerard; US2014/275082; (2014); A1;,
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Adding a certain compound to certain chemical reactions, such as: 369-26-6, name is Methyl 3-amino-4-fluorobenzoate, 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 369-26-6, Computed Properties of C8H8FNO2

To the solution of compound 7-bromoimidazo[1,2-a]pyridine-3-carboxylic acid (Intermediate 1) (1.26 Kg, 5.23 mol) in DMAC (15 L) was added dropwise SOCl2 (1.86 kg, 15.6 mol) at 10 °C in 30 min. To the resulting mixture warmed to 20°C was added compound methyl 3-amino-4-fluorobenzoate (884 g, 5.23 mol) in DMAC (3.0 L) over 30 min. After addition, the reaction temperature went up to 30 °C. HPLC showed the reaction went to completion within 5 min. To the reaction mixture was added water (20 L) over 20 min. The mixture was filtered and dried under vacuum to afford the title compound as a white solid; 1 H NMR (400 MHz, DMSO-d6) delta 3.87 (s, 3 H) 7.57 (dd, J=7.28, 2.01 Hz, 1 H) 7.51 (dd, J=10.16, 8.66Hz, 1 H) 7.90 (td, J=4.33, 2.38 Hz, 1 H) 8.29 (m, 2H) 8.90 (s, 1 H) 9.43 (d, J=7.53 Hz, 1 H) 10.78 (s, 1 H) Rt 6.90 mins; MS m/z 394.0 {M+H}+; Method 10 min LC

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; NOVARTIS AG; BRUCE, Ian; CHAMOIN, Sylvie; COLLINGWOOD, Stephen Paul; FURET, Pascal; FURMINGER, Vikki; LEWIS, Sarah; LOREN, Jon; LV, Lin; MOLTENI, Valentina; SAUNDERS, Alex Michael; SHAW, Duncan; TURNER, Roy; YEH, Vince; WO2014/132220; (2014); A1;,
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Synthetic Route of 59833-69-1,Some common heterocyclic compound, 59833-69-1, name is Methyl 2-(3-amino-4-chlorophenyl)acetate, molecular formula is C9H10ClNO2, 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 stirred solution of 12e (62 mg, 0.4 mmol) in CH2Cl2 (5 mL) were added a solution of 18 (133 mg, 0.4 mmol) in CH2Cl2 (3 mL) and then pyridine (0.067 mL, 0.8 mmol). After stirring overnight at room temperature, the reaction mixture was diluted with water and extracted with EtOAc (×2). The combined organic layers were washed with 1 M NaOH aq, water, brine, dried over Na2SO4 and concentrated in vacuo. The resulting residue was purified by column chromatography on silica gel to yield methyl ester (120 mg, 63%); TLC Rf = 0.14 (n-hexane/EtOAc, 7:3); 1H NMR (300 MHz, CDCl3) delta 7.60-7.38 (m, 4H), 7.32 (t, J = 7.8 Hz, 1H), 7.06 (d, J = 7.5 Hz, 1H), 6.92-6.77 (m, 4H), 6.74-6.66 (m, 2H), 4.70-4.60 (m, 1H), 4.26 (dd, J = 9.6, 5.4 Hz, 1H), 4.14 (dd, J = 11.4, 6.6 Hz, 1H), 3.71 (s, 3H), 3.65 (s, 2H), 3.39 (dd, J = 11.4, 3.0 Hz, 1H), 3.26 (dd, J = 11.4, 7.8 Hz, 1H), 2.91 (s, 3H), 2.51 (s, 3H).CommentTo a stirred solution of methyl ester (120 mg, 0.25 mmol) described above in MeOH (4 mL) and THF (4 mL) was added 5 M NaOH aq (2 mL). After stirring for 1 h at room temperature, the reaction mixture was diluted with 2 M HCl aq and extracted with EtOAc (×2). The combined organic layers were washed with water, brine, dried over Na2SO4 and concentrated in vacuo to give a crude product, which was washed with EtOAc/n-hexane to yield 4a (85 mg, 73%) as a pale blue powder

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 2-(3-amino-4-chlorophenyl)acetate, its application will become more common.

Reference:
Article; Iwahashi, Maki; Takahashi, Eiji; Tanaka, Motoyuki; Matsunaga, Yoko; Okada, Yutaka; Matsumoto, Ryoji; Nambu, Fumio; Nakai, Hisao; Toda, Masaaki; Bioorganic and Medicinal Chemistry; vol. 19; 18; (2011); p. 5361 – 5371;,
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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. 35120-18-4, name is Ethyl 1-bromocyclobutanecarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of Ethyl 1-bromocyclobutanecarboxylate

A) Ethyl 1-azidocyclobutane-1 -carboxylate: To a flask was added ethyl 1-bromocyclobutane-1-carboxylate (5.0 g, 25 mmol), dimethylformamide (120 mL), and sodium azide (2.43 g, 37.5 mmol). After stirring at room temperature for 2 days, the reaction was taken up in ether and washed with water (3 x 150 mL). The organic layer was removed and dried over magnesium sulfate. The drying reagent was removed by vacuum filtration and the solvent removed by rotary evaporator to give a colorless liquid, 3.69 g, yield 87%. 1H-NMR (CDCl3) delta 1.29 (t, 3H), 2.00 (m, 2H), 2.25 (m, 2H), 2.55 (m, 2H), 4.22 (q, 2H); IR (neat) 2109 cm-1.

The synthetic route of 35120-18-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Products Inc.; EP952148; (1999); A1;,
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