Tag: M.W=200-300

Related Products of 36805-97-7,Some common heterocyclic compound, 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, molecular formula is C11H25NO2, 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.

Hexadecanedioic acid (4.5 g, 15.71 mmol) was suspended in Toluene (28.1 ml) and the mixture was heated to reflux. 1,1 -di-tert-butoxy-N,Ndimethylmethanamine (10.10 ml, 42.1 mmol) was added drop-wise over 30 mm. Themixture was reflux overnight. The solvent was removed in vacuo at 50C and the crude material was suspended in CH2C12/EtOAc (75 mL. 1:1) ans stirred for 15 mm. The solids were removed by filtration and washed with CH2C12 (25 mL). The filtration was evaporated in vacuo. The resulting material was suspended in CH2C12 (6 mL), cooled with ice for 10 mins, and filtered. The solvent was removed invacuo to leave crude product which was purified by flash chromatography (silic gel,EtOAc/Hexane) to get 16-(tert-butoxy)-16-oxohexadecanoic acid (2.56 g, 7.47 mmol,47.6 % yield). Analysis condition D: Retention time = 5.04 mm; ESI-MS(+) m/z269.3 [M – OC(CH3)3]; ?H NMR (500MHz, METHANOL-d4) oe 2.33 – 2.18 (m, 4H),1.66 – 1.54 (m, 4H), 1.50 – 1.43 (m, 9H), 1.40 – 1.25 (m, 20H).

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

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; GILLMAN, Kevin W.; GOODRICH, Jason; BOY, Kenneth M.; ZHANG, Yunhui; MAPELLI, Claudio; POSS, Michael A.; SUN, Li-Qiang; ZHAO, Qian; MULL, Eric; GILLIS, Eric P.; SCOLA, Paul Michael; LANGLEY, David, R.; (683 pag.)WO2016/77518; (2016); A1;,
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Related Products of 13321-74-9, 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. 13321-74-9, name is 4-Bromo-2,5-dimethoxytoluene, This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of 1-bromo-2,5-dimethoxy-4-methylbenzene (12) (1.98 g, 8.58 mmol) and (R)-3-acryloyl-4-phenyloxazolidin-2-one (13) (1.86 g, 8.58 mmol) in MeCN/H2O (10:1, 40 mL) were added Pd(OAc)2 (192.58 mg, 0.86 mmol), (o-tol)3P (522 mg, 1.7 mmol), and Et3N (2.391 mL, 0.017 mmol) at rt, and allowed to warm to 80 C. After being stirred at the same temperature for 2 h, the resultant mixture was added water and CH2Cl2 and then extracted with CH2Cl2. The combined extracts were washed with brine, the residue upon workup was chromatographed on silica gel with hexane/AcOEt (4:1 v/v) as a eluent to give a enone 5 (2.564 g, 81%) as a yellow solid; inlMMLBox -5.17 (c 0.95 in CHCl3); mp 55.5-59.5 C; IR (neat) 2958, 1781, 1705, 1505, 1465, 1384, 1209, 1045 cm-1; 1H NMR (400 MHz, CDCl3) delta 2.24 (3H, s), 3.82 (3H, s), 3.82 (3H, s), 4.31 (1H, dd, J=8.8 and 4.0 Hz), 4.73 (1H, t, J=8.8 Hz), 5.57 (1H, dd, J=8.8 and 4.0 Hz), 6.72 (1H, s), 7.02 (1H, s), 7.30-7.39 (5H, m), 7.93 (1H, d, J=16.0 Hz), 8.12 (1H, d, J=16.0 Hz); 13C NMR (100 MHz, CDCl3) delta 16.7 (CH3), 55.8 (CH3), 56.0 (CH3), 57.8 (CH3), 69.8 (CH2), 109.8 (CH), 114.4 (CH), 115.7 (CH), 121.1 (Cq), 125.9 (CH), 128.5 (CH), 129.0 (CH), 131.8 (Cq), 139.3 (Cq), 142.0 (CH), 151.7 (Cq), 153.0 (Cq), 153.9 (Cq), 165.2 (Cq); HRMS (ESI) calcd for C21H21NO5Na [M+Na]+ 390.1317, found 390.1310.

The chemical industry reduces the impact on the environment during synthesis 4-Bromo-2,5-dimethoxytoluene. I believe this compound will play a more active role in future production and life.

Reference:
Article; Miyawaki, Akari; Osaka, Mayu; Kanematsu, Makoto; Yoshida, Masahiro; Shishido, Kozo; Tetrahedron; vol. 67; 35; (2011); p. 6753 – 6761;,
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Electric Literature of 31465-36-8, These common heterocyclic compound, 31465-36-8, name is 4-(4-Methoxyphenoxy)aniline, 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: A mixture of a 3{1,1} (1.4 g, 5.53 mmol) and phenyl isothiocyanate (1.08 mL, 8.27 mmol) in anhyd DMF (8.0 mL) was stirred at room temperature for 6-7 h. Thereafter the reaction mixture was diluted with 50 mL H2O and extracted with EtOAc (4 x 20 mL). The combined organic layer was dried over anhyd Na2SO4, concentrated and the residue thus obtained was purified through silica-gel column chromatography using EtOAc-Hexanes (70-90:30-10, v/v) as eluent to yield 4{1,1,1} as a white solid (1.7 g, 80%).

The synthetic route of 31465-36-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mishra, Amita; Batchu, Harikrishna; Srivastava, Kumkum; Singh, Pratiksha; Shukla, Pravin K.; Batra, Sanjay; Bioorganic and Medicinal Chemistry Letters; vol. 24; 7; (2014); p. 1719 – 1723;,
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37895-73-1, name is 1,2-Dibromo-4,5-dimethoxybenzene, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. HPLC of Formula: C8H8Br2O2

A flask containing 4,5-dibromoveratrole (500 mg, 1.69 mmol), 4-fluorophenylboronic acid (946 mg, 6.76 mmol), Pd(OAc)2 (38 mg, 0.169 mmol), XPhos (161 mg, 0.338 mmol), and K2CO3 (1.4 g, 10.1 mmol) was degassed and dioxane (10 mL) and H2O (5 mL) were added. Reaction was refluxed at 102 C. overnight then cooled to RT and diluted with EtOAc. Solution was washed with saturated NaHCO3 solution followed by brine and organic layer was collected, dried over Na2SO4, and concentrated. Chromatography using ISCO max gradient 10% EtOAc/hexane yielded product as a white solid (525 mg, 95% yield); 1H NMR (400 MHz) (CDCl3) delta 7.12-7.08 (m, 4H), 6.96-6.91 (m. 6H), 3.97 (s, 6H); 13C NMR (100 MHz) (CDCl3) delta 161.6 (JC,F=244 Hz), 148.4, 137.3 (JC,F=3 Hz), 132.1, 131.4 (JC,F=8 Hz), 114.9 (JC,F=21 Hz), 113.6.

The synthetic route of 37895-73-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY; LaVoie, Edmond J.; Arnold, Eddy; Bauman, Joseph D.; Kerrigan, John E.; Parhi, Ajit K.; Das, Kalyan; Kelley, Cody; Patel, Dishaben V.; US2015/322022; (2015); A1;,
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Synthetic Route of 27060-75-9, 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. 27060-75-9, name is 1-Bromo-4-methoxy-2-methylbenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 1. Synthesis of 1-(4-methoxy-2-methylphenyl)propan-2-one (C8) Four batches of this experiment were carried out (4*250 g substrate). Tributyl(methoxy)stannane (400 g, 1.24 mol), 1-bromo-4-methoxy-2-methylbenzene (250 g, 1.24 mol), prop-1-en-2-yl acetate (187 g, 1.87 mol), palladium(II) acetate (7.5 g, 33 mmol) and tris(2-methylphenyl)phosphane (10 g, 33 mmol) were stirred together in toluene (2 L) at 100 C. for 18 hours. After cooling to room temperature, the reaction mixture was treated with aqueous potassium fluoride solution (4 M, 400 mL) and stirred for 2 hours at 40 C. The resulting mixture was diluted with toluene (500 mL) and filtered through Celite; the filter pad was thoroughly washed with ethyl acetate (2*1.5 L). The organic phase from the combined filtrates was dried over sodium sulfate, filtered, and concentrated in vacuo. Purification via silica gel chromatography (Gradient: 0% to 5% ethyl acetate in petroleum ether) provided the product as a yellow oil. Combined yield: 602 g, 3.38 mol, 68%. LCMS m/z 179.0 [M+H+]. 1H NMR (400 MHz, CDCl3) delta 7.05 (d, J=8.3 Hz, 1H), 6.70-6.77 (m, 2H), 3.79 (s, 3H), 3.65 (s, 2H), 2.22 (s, 3H), 2.14 (s, 3H).

The synthetic route of 1-Bromo-4-methoxy-2-methylbenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC; DAVOREN, JENNIFER ELIZABETH; DOUNAY, AMY BETH; EFREMOV, IVAN VIKTOROVICH; GRAY, DAVID LAWRENCE FIRMAN; MENTE, SCOT RICHARD; O’NEIL, STEVEN VICTOR; ROGERS, BRUCE NELSEN; SUBRAMANYAM, CHAKRAPANI; ZHANG, LEI; US2014/128374; (2014); A1;,
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Related Products of 588-63-6, 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. 588-63-6, name is (3-Bromopropoxy)benzene, This compound has unique chemical properties. The synthetic route is as follows.

Scheme IV, Step S: Synthesis of 1-(3-phenoxy-propyl)-piperidine (Scheme IV, Compound 4) Mix 3-phenoxypropyl bromide (801.5 g, 3.73 mol), potassium iodide (61.8 g, 0.37 mol, 0.10 equivalents) and water (4.0 L) in a 12-L, 3-necked flask fitted with: a stirrer, thermometer in a side-arm adapter, connected to a Firestone.(R). valve and an addition funnel fitted with a gas outlet adapter, connected to a bubbler. Add piperidine (634.6 g, 7.45 mol, 2.0 equivalents) over 1 hour, without cooling under nitrogen. The temperature at the end of the addition is 40°C. Heat the reaction mixture and maintain the temperature at 50°C for 6 hours. Monitor the progress of the reaction by HPLC (Column=300 x 3.9 mm Phenomenex Bondclone 10 CN; mobile phase=65percent acetonitrile:35percent 0.1N ammonium formate buffer; flow=1.5 mUminute; wavelength=215 nm; RT: 3-phenoxypropyl bromide=2.3 minutes; 37=4.4 minutes). Typically, the conversion is 94percent. Cool the reaction mixture to ambient temperature over a time period of 14 hours and extract with dichloromethane (2 x 4.0 L). Combine the organic extracts and dry over MgSO4 (400 g). Filter off the drying agent and wash with dichloromethane (1.0 L). Concentrate the filtrate (35-40 °C/50 torr) to give 800 g, 98percent Yield) of 4, as an oil. HPLC analysis shows that 37 is 90percent pure. Purify 4 (16.5 g portion) by distillation under vacuum and collect the title compound (10 g) as a colorless liquid at 99-105°C/0.3 mm: 1H NMR (CDCl3, 200MHz) delta 1.38-1.5 (m, 2H), 1.5-1.64 (m, 4H), 1.9-2.1 (m, 6H), 4.0 (t, 2H), 6.85-6.95 (m. 3H), 7.22-7.3 (t, 2H). Analysis calculated for C14H21NO: C, 76.67; H, 9.65; 6.39. Found: C, 76.55; H, 9.50; N, 6.22. [M+H]+=220 m/e.

The chemical industry reduces the impact on the environment during synthesis (3-Bromopropoxy)benzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Aventis Pharmaceuticals Inc.; EP1216244; (2003); B1;,
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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. 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C10H13BrO

[(3-Benzyloxy-propyl)-ethoxy-phosphinoylmethyl]-phosphonic acid diethyl ester: To an oven-dried flask was added 10.25 g (44.7 mmol) of (3-Bromo-propoxymethyl)-benzene and 7.67 mL (44.7 mmol) of triethyl phosphite. The flask was fitted with a short-path distillation head, for removal of bromoethane, and the mixture heated at 150° C. for 4 h. The reaction was cooled to ambient temperature, and then diluted with 120 mL of absolute ethanol and 1.8 N KOH (120 mL, 216 mol). The distillation head was replaced with a reflux condenser and the solution heated at reflux for 5 h. The reaction was cooled then concentrated in vacuo. The basic aqueous layer was extracted with EtOAc (2*) and then acidified to pH 3 with conc. HCl. The aqueous layer was extracted with EtOAc (3*) and the combined extracts were dried over MgSO4 and concentrated. The resulting crude product (8.24 g) was used as is in the next reaction. 31P NMR (300 MHz, DMSO-d6) delta34.113.

The synthetic route of 54314-84-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wang, Yihan; Metcalf III, Chester A.; Shakespeare, William C.; Sawyer, Tomi K.; Bohacek, Regine; US2003/100573; (2003); A1;,
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Reference of 588-96-5, A common heterocyclic compound, 588-96-5, name is p-Bromophenetole, molecular formula is C8H9BrO, 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 XII.1 (S)-(1-{4-[1-(4-Ethoxy-phenyl)-piperidin-4-yl]-phenyl}-ethyl)-carbamic acid tert-butyl ester 6.21 g (19.1 mmol) cesium carbonate are added to a mixture of 5.80 mg (19.1 mmol) (S)-[1-(4-piperidin-4-yl-phenyl)-ethyl]-carbamic acid tert-butyl ester (V.5), 4.21 g (21.0 mmol) 1-bromo-4-ethoxy-benzene, 454 mg (0.953 mmol) X-Phos and 214 mg (0.953 mmol) palladium(II) acetate in 50 mL toluene/10 mL tert-butanol. The mixture is stirred for 3 h at 120 C. under inert gas atmosphere. After that time, the mixture is poured into water and extracted with ethyl acetate. The organic layer is washed with water and dried over magnesium sulphate. The solvent is removed in vacuo and the residue is recrystallized from acetonitrile. C26H36N2O3 (M=424.6 g/mol) ESI-MS: 425 [M+H]+

The synthetic route of 588-96-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2012/157425; (2012); A1;,
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Application of 3401-47-6, 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. 3401-47-6 name is 1-Bromo-2-methoxynaphthalene, 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.

In a glove box, 1.0 mmol of 1-bromo-2-methoxynaphthalene, 2.0 mmol of aryl boronic acid, Pd2 (dba) 3, phosphine ligand and 3.0 mmol of potassium phosphate were charged in 7 mL of anhydrous toluene under nitrogen , And the temperature was raised to 80 C, and the reaction was carried out for a period of time. The results are shown in Table 2 below.The amount of Pd2 (dba) 3 and the phosphine ligand is divided into two kinds: (1) 0.25 mol% Pd2 (dba) 3, 0.5 mol% phosphine ligand, or (2) 0.5 mol% Pd2 (dba) mol% phosphine ligand, depending on the amount of ligand used in Table 2.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-2-methoxynaphthalene, and friends who are interested can also refer to it.

Reference:
Patent; Sun Yat-sen University; Qiu Liqin; Yu Sifan; Zhou Xiantai; (23 pag.)CN106995461; (2017); A;,
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Some common heterocyclic compound, 156573-09-0, name is 1-Bromo-4-ethoxy-2,3-difluorobenzene, molecular formula is C8H7BrF2O, 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. HPLC of Formula: C8H7BrF2O

First Step THF (100 ml) was added to 1-bromo-4-ethoxy-2,3-difluorobenzene (5.1 g) in a reaction vessel under an atmosphere of nitrogen, and the mixture was cooled to -78 C. n-Butyllithium (1.57 M, in a hexane solution) (13.8 ml) was added dropwise at a temperature of -70 C. or lower. The stirring was continued at -78 C. for another 2 hours, and 4-(3-propylcyclopentyl)-cyclohexanone (3.0 g) in a THF (10 ml) solution was added dropwise at a temperature of -70 C. or lower. After the mixture had been stirred at -78 C. for another 1 hour, it was warmed to room temperature, and a saturated aqueous solution of ammonium chloride (50 ml) was added. The mixture was separated, and the water layer was extracted with ethyl acetate three times, and then the combined organic layer was washed with brine. The solution was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (eluent: ethyl acetate/n-heptane= 1/9 by volume) to give 1-(4-ethoxy-2,3-difluorophenyl)-4-(3-propylcyclopentyl)cyclohexanol (5.0 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 156573-09-0, its application will become more common.

Reference:
Patent; CHISSO PETROCHEMICAL CORPORATION; JNC CORPORATION; US2011/309300; (2011); A1;,
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