Tag: M.W=200-300

Adding a certain compound to certain chemical reactions, such as: 168268-00-6, name is 4-(Benzyloxy)-3-fluoroaniline, belongs to ethers-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 168268-00-6, name: 4-(Benzyloxy)-3-fluoroaniline

A solution of 1.23 L of acetone and 600 ml of water in sodium carbonate (132 g, 1.25 mol) was added to the oil and thenCool down to 05C, add benzyl chloroformate (127.8g, 0.748mol) dropwise, continue stirring for 15min,Filtration gave 133 g of a yellow solid as a compound of formula (4) with a yield of 98.9%.

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; Shanghai Pharmaceutical Industry Institute; China Pharmaceutical Industry Zongyuan; Li Jianqi; Zeng Huang; Zhang Zixue; Liu Yu; Pan Deng; Zou Lei; Zhang Yi; (8 pag.)CN108069919; (2018); A;,
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Reference of 36805-97-7, 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. 36805-97-7 name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, 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.

Example 10 2′-(6-Carbamimidoyl-1-methyl-1H-indol-3-ylmethyl)-4-methoxy-5′-methylcarbamoyl-biphenyl-2-carboxylic acid; Part A. 3-bromo-4-formyl-benzoic acid tert-butyl ester:; A solution of 3-bromo-4-methylbenzoic acid (5 g, 0.023 mol) in 40 mL toluene was heated to 80 C. in an oil bath and DMF-di-t-butylacetal (22.4 ml, 0.093 mol) was added dropwise over 20 min. The resulting mixture was heated for an additional 1 h and then cooled to rt and evaporated to dryness. Chromatography on silica gel (hexane/ethyl acetate 1:1) provided the t-butyl ester (5.1 g, 81%) which was dissolved in 50 mL CCl4 and treated with N-bromosuccinimide (6.7 g, 0.037 mol) and benzoylperoxide (0.22 g, 0.94 mmol). The mixture was then heated in an 80 C. oil bath overnight. Solvent was removed by evaporation, and residue was taken up in EtOAc and washed with water, sat’d Na2CO3 and brine then dried over anh. Na2SO4, filtered and concentrated. Chromatography on silica gel (hexane/ethyl acetate 1:1) provided the dibromide (7.5 g, 94%) to which was added 30 mL morpholine and the mixture was heated overnight at 60 C. After cooling to rt, the mixture was diluted with EtOAc and washed with 5% citric acid solution until aqueous phase stays at pH 4, then with sat’d bicarbonate solution and brine. Organic phase was dried and concentrated to provide the aldehyde in 74% yield after flash chromatography. 1NMR (500 MHz, CDCl3) delta 10.40 (s, 1H); 8.24 (s, 1H); 7.95 (m, 1H); 7.93 (m, 1H); 1.61 (s, 9H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, and friends who are interested can also refer to it.

Reference:
Patent; Smallheer, Joanne M.; Corte, James R.; US2005/228000; (2005); A1;,
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Electric Literature of 37895-73-1,Some common heterocyclic compound, 37895-73-1, name is 1,2-Dibromo-4,5-dimethoxybenzene, molecular formula is C8H8Br2O2, 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 Schlenk tube (20 mL) were added PdCl2(MeCN)2 (26 mg, 0.10 mmol) and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (SPhos, 0.16 g, 0.40 mmol). The Schlenk tube was capped with a rubber septum and then evacuated and purged with argon. The evacuation-purge operation was repeated twice. To the tube was added 1,4-dioxane (6.0 mL), 1,2-dibromobenzene (1.63 g, 0.82 mL, 5.0 mmol), NEt3 (3.04 g, 4.18 mL, 30.0 mmol), and pinacolborane (2.18 mL, 1.92 g, 15.0 mmol) in this order with syringes, respectively, through the septum. The reaction mixture was heated at 110 C and the progress of the reaction was monitored by gas chromatography. After the complete consumption of the dibromide was confirmed, the reaction mixture was then allowed to cool to room temperature. The resulting solution was filtered through a thin pad of Celite with EtOAc as the eluent. The organic solvent was removed under reduced pressure to give the crude product, which was purified by column chromatography on silica gel followed by recrystallization from hexane at -20 C, giving rise to 1,2-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene (3h, 0.83 g, 51%) as a colorless solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,2-Dibromo-4,5-dimethoxybenzene, its application will become more common.

Reference:
Article; Shimizu, Masaki; Nagao, Ikuhiro; Tomioka, Yosuke; Kadowaki, Tsugumi; Hiyama, Tamejiro; Tetrahedron; vol. 67; 41; (2011); p. 8014 – 8026;,
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Some common heterocyclic compound, 36449-75-9, name is 1-(2-Bromoethyl)-2-methoxybenzene, molecular formula is C9H11BrO, 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 C9H11BrO

b) At rt, a solution of 1-(2-bromo-ethyl)-2-methoxy-benzene (1.0 g, 4.15 mmol) inabs. THF (5 mL) is added to Mg turnings (0.13 g, 5.35 mmol) suspended in abs.THF (5 ml) over a period of 20 min. The thus obtained Grignard reagent is then added at to an ice-cold solution of (1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid methoxy-methyl-amide (400 mg, 1.5 mmol) in THF (5 ml). The reaction mixture is stirred at rt for 1 h, quenched by adding sat. aq. NhUCI (10 ml_), diluted with water (100 ml) and extracted twice with DCM (100 ml_). The combined organic extracts are dried over NaaSO/j, filtered and evaporated . The resulting residue is purified by prep. HPLC to afford 3-(2-methoxy-phenyl)-1-((1aS,5aR)-1,1,2~trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]penta-len-4-yl)-propan-1-one (390 mg) as a colourless oil. LC-MS: tR = 1.15 min, [M+1f = 341.21; 1H NMR (CDCI3): 8 7.22-7.14 (m, 2H), 6.90-6.81 (m, 2H), 3.82 (s, 3H), 3.20-2.90 (m, 5H), 2.79 (d, J = 18.8 Hz, 1H), 2.38 (s, 3H), 1.88 (d, J = 2.9 Hz, 2H), 1.12 (s, 3H), 0.72 (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 36449-75-9, its application will become more common.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD.; WO2006/10379; (2006); 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. 20469-65-2, name is 1-Bromo-3,5-dimethoxybenzene, A new synthetic method of this compound is introduced below., Formula: C8H9BrO2

Example 28 Synthesis of 1-Bromo-3,5-dihydroxybenzene (33) [0118] 1-bromo-3,5-dimethoxybenzene (32) (1.00 g, 4.60 mmol) was dissolved in dry dichloromethane (40 ml) and cooled in an ice bath. Boron tribromide (1.33 ml, 13.82 mmol) was added and the mixture was stirred on 2 h. The mixture was allowed to warm up to room temperature and stirred overnight. Methanol (1.4 ml) was added drop-wise to terminate the reaction, and the mixture was poured into water (50 ml) and stirred at RT for 2 h. Reaction mixture was neutralized with NaHCO3 and the mixture extracted twice with ethyl acetate (30 ml). Combined organic layers were dried over Na2SO4 and evaporated to dryness. Product was purified by column chromatography using silica gel as stationary phase and methanol:dichloromethane (5:95) as eluent. Product was a white solid. Yield: 0.71 g (81%). 1HNMR (DMSO-d6, delta ppm): 9.68 (2H, s), 6.38 (2H, d, J=2 Hz), 6.19 (1H, dd, J=2 Hz).

The synthetic route of 20469-65-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DHR Finland OY; Meltola, Niko; Takalo, Harri; Sund, Henri; US2013/183771; (2013); A1;,
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Synthetic Route of 934240-59-2, These common heterocyclic compound, 934240-59-2, name is 1-((4-Bromophenoxy)methyl)-2-fluorobenzene, 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.

Description 2j Methyl (2SV2-r(te/f-butoxycarbonvnaminol-5-f4-r(2- fluorobenzyl)oxylphenyl)-5-oxopentanoate (D2)To a stirred suspension of magnesium metal (9Og) in dry THF (60OmL) under a nitrogen atmosphere at room temperature was added iodine (0.3g). The mixture was heated to an internal temperature of 63-65C. A solution of 1-[(4- bromophenoxy)methyl]-2-fluorobenzene (D1 , 693g) in THF (150OmL) was added in two batches, firstly 45 mL was added in one go. Secondly, the remaining solution (1500 mL) was added dropwise. After addition, the reaction was heated at reflux for 1 h. The reaction mixture was cooled to room temperature. This reaction mixture was then added slowly to a solution of 1-te/f-butyl 2-methyl (2S)-5-oxopyrrolidine-1 ,2- dicarboxylate (ISOCHEM, 30Og) in THF (150OmL) cooled to -6OC, maintaining the internal temperature below -60C. The addition was completed in 1.25 hours. The reaction mixture was stirred for a further 1 hour after addition, lsopropyl alcohol (30OmL) was then added drop-wise whilst maintaining the temperature below -60C. A mixture of aqueous saturated ammonium chloride solution/aqueous saturated sodium chloride solution (2/1 ; 90OmL) was added whilst maintaining the temperature at -50C. Water (600 mL) was added to dissolve the yellow precipitate. The organic phase was separated and was washed with aqueous 13% NaCI solution (60OmL). The organic phase was concentrated to dryness. EtOAc (150OmL) was then added and the solution was evaporated under reduced pressure to remove water. The residue was purified by chromatography on silica gel eluting with cyclohexane / ethyl acetate (95:5 to 8:2) to afford the title compound (287 g); 1H NMR (600 MHz, DMSO- d6) ?(ppm): 7.93 (d, 2H); 7.57 (td, 1 H); 7.44 (m, 1 H); 7.27 (m, 3H); 7.14 (d, 2H); 5.24 (s, 2H); 4.04 (m, 1 H); 3.61 (s, 3H); 3.03 (m, 2H); 1.94 (m, 2H); 1.38 (s, 9H).

The synthetic route of 934240-59-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/122546; (2008); A1;,
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Adding a certain compound to certain chemical reactions, such as: 74137-36-3, name is 1,3-Dibromo-5-methoxybenzene, belongs to ethers-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 74137-36-3, Quality Control of 1,3-Dibromo-5-methoxybenzene

General procedure: 2-Ethylhexyl 3-((3-bromo-5-methoxyphenyl)thio)propanoate was synthesised according to general procedures GP12 – from 1 ,3-dibromo-5-methoxybenzene (3.0 g, 1 1 .3 mmol), Pd2(dba)3 (0.25 mg, 2.5 mol%), Xantphos (0.32 mg, 5 mol%), 2-ethylhexyl-3-mercaptopropionate (1 .96 g, 9.02 mmol), DIPEA (4.15 ml_, 23.9 mmol) and toluene (30 ml_); 1 10 C, 8 h. Chromatography (12% EtOAc in hexane) afforded a pale orange solid (2.4 g, 66%). NMR (400 MHz, DMSO-c/6) delta 7.05 (t, J = 1 .6 Hz, 1 H), 6.99 (d, J = 2.0 Hz, 1 H), 6.87 (t, J = 2.0 Hz, 1 H), 3.95 (d, J = 5.6 Hz, 2H), 3.76 (s, 3H), 3.21 (t, J = 6.4 Hz, 2H), 2.63 (t, J = 6.8 Hz, 2H), 1 .52-1 .50 (m, 1 H), 1 .29-1 .24 (m, 8H), 0.87-0.82 (m, 6H). LCMS (ESI, -ve) m/z 217/219 (M-C11 H21O2)-. General procedures GP12 00690] Condition A – a mixture of bromide GP12_1 , Pd2(dba)3 (5 mol%), Xantphos (10 mol%), RSH (1 .0-1 .2 equiv.), NaO’Bu (1 .0-1 .2 equiv.) and ‘BuOH/toluene (1 :5) was degassed with argon and then stirred at 100 C for 16 h. After cooling to rt, the suspension was filtered through celite, washed with DCM and the solvent was removed under reduced pressure. Alternatively, the mixture was centrifuged at 2500 RPM for 5 minutes. The solution was decanted and concentrated under reduced pressure. The crude was purified by chromatography to afford sulfide GP12_2. (1128) [00691] Condition B – same as condition A, with DIPEA used instead of NaO’Bu and toluene used instead of ‘BuOH/toluene.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,3-Dibromo-5-methoxybenzene, and friends who are interested can also refer to it.

Reference:
Patent; THE INSTITUTE OF CANCER RESEARCH: ROYAL CANCER HOSPITAL; SPRINGER, Caroline; MARAIS, Richard; NICULESCU-DUVAZ, Dan; LEUNG, Leo; SMITHEN, Deborah; CALLENS, Cedric; TANG, Haoran; (403 pag.)WO2017/141049; (2017); A1;,
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2674-34-2, name is 1,4-Dibromo-2,5-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. category: ethers-buliding-blocks

1, 4-diamino -2, 5- […] (1, 4-diamino-2, 5-dimethoxybenzene) (16.9mmol) and 30 parts by weight of diethyl ether (70 ml) at -78 C 1.55N of agitating n-BuLi (16.8mmol) in 11 ml of hexane of. input additional are mixed together. 1.5 in the maintaining -78 C mixture adaptation stirring time. Dichloro d methyl thread column (8.4mmol) and 30 parts by weight of diethyl ether in the -78 C a 2 ml is closed after charging additional adaptation stirring during night at room temperature. After 1.5 reflux time was are input, in water and and stirring. possibility layer hexane and water extraction of water and balancer in a washing machine after the washing phosphorous in the magnesium sulfate expresses water after to remove, is every. D-1 compounds via fractional distillation (45% yield) is obtained.

The synthetic route of 2674-34-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LG DISPLAY CO., LTD.; SIN, IN AEY; LEE, SUNG JAE; BIN, JONG KWAN; LEE, BANG SOOK; SAW, BO MIN; YU, YOUNG JU; (45 pag.)KR2015/64794; (2015); A;,
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Reference of 19056-40-7, 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. 19056-40-7, name is 4-Bromo-3-methoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To an ice cooled solution of 4-bromo-3-methoxyaniline (3.00 g, 14.85 mmol) in pyridine(20 mL) was added (E/Z)-3-ethoxyacryloyl chloride (2.98 g, 22.27 mmol) over a period of 5 mm.and stirred at RT for 16 h. After completion of the reaction, the reaction mixture was diluted with ice cooled water and extracted with EtOAC (150 mL x 2). The combined organic layer was washed with aq. iN HC1 (100 mL), water (150 mL), brine (100 mL), dried over sodium sulphate and concentrated. The residue was used for next step without further purification (3.20 g, 72percent).1H NMR (400 MHz, DMSO-d6): oe 9.86 (s, 1H), 7.54?7.42 (m, 3H), 7. 12?7.08 (m 1H), 5.50 (d,J=12.7 Hz, 1H), 3.95 (q, J=6.9 Hz, 2H), 3.80 (s, 3H), 1.27 (t, J=7.3 Hz, 3H); LC-MS: mlz 301.1(M+1).

The synthetic route of 4-Bromo-3-methoxyaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; SAMAJDAR, Susanta; ABBINENI, Chandrasekhar; SASMAL, Sanjita; HOSAHALLI, Subramanya; WO2015/104653; (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. 4698-11-7, name is 10-Methoxy-5H-dibenzo[b,f]azepine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 4698-11-7

Following the procedure of Example 1, but using 30% aqueous formic acid instead of the same volume of 10% aqueous sulfuric acid, the yield is 58.0 (76.6% on theoretical).

The synthetic route of 4698-11-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Milanese, Alberto; EP1600443; (2005); A1;,
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