Tag: M.W=200-300

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 175278-09-8 as follows. Formula: C7H5BrF3NO

A solution of 8 g (31 mmol) of 4-bromo-2-trifluoromethoxyaniline and 4.2 g (37.5 mmol) of DABC (triethylenediamine) in 40 mL of toluene was slowly added dropwise 7 mL of carbon disulfide and the reaction was stirred at room temperature 8h. After the reaction, the reaction solution was suction filtered, and the filter cake was 3g of [4-bromo-2-trifluoromethoxyphenyl] dithioic acid with a yield of about 28%.

According to the analysis of related databases, 175278-09-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Xi’an Jiao Tong University; He, LangChong; Zhang, Jie; Pan, XiaoYan; Wang, Jinfeng; Su, Ping; Lu, Wen; Wang, Sicen; (17 pag.)CN105924385; (2016); A;,
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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. 204452-91-5, name is 7-(Dimethoxymethyl)-1,2,3,4-tetrahydro-1,8-naphthyridine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C11H16N2O2

[0567] A solution of7 -( dimethoxymethyl)-1,2,3,4-tetrahydro-1,8-naphthyridine (intermediate 4, 2 g, 9.60 mmol) anddiphenylcarbonate ( 4.11 g, 19.21 mmol) in THF ( 40 ml) at-15 C. was treated with LHMDS (1M in THF, 13.3 ml, 13.3mmol) over 0.5 h. The reaction mixture was quenched withsat. aq. NH4Cl, extracted with EtOAc (2x). The combinedorganic layers were washed with brine, dried over Na2S04 ,filtered and concentrated under reduced pressure. The crudeproduct was purified by normal phase chromatography (80 gsilica gel cartridge, heptanes/EtOAc 100:0 to 25:75) to givethe title compound as a pale yellow solid. 1H-NMR (400MHz, DMSO-d6 ) o7.65 (d, lH), 7.46-7.38 (m, 2H), 7.27-7.18 (m, 4H), 5.17 (s, lH), 3.87-3.80 (m, 2H), 3.26 (s, 6H), 2.83(t, 2H), 2.00-1.92 (m, 2H).

The synthetic route of 204452-91-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Novartis AG; Buschmann, Nicole; Fairhurst, Robin Alec; Furet, Pascal; Knoepfel, Thomas; Leblanc, Catherine; Liao, Lv; Mah, Robert; Nimsgern, Pierre; Ripoche, Sebastien; Xiong, Jing; Han, Bo; Wang, Can; Zhao, Xianglin; US2015/119385; (2015); A1;,
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Some common heterocyclic compound, 95970-08-4, name is 2,5-Dibromoanisole, molecular formula is C7H6Br2O, 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. COA of Formula: C7H6Br2O

(0957) [00336] Into a lOG-mL round-bottom flask, purged and maintained under an inert atmosphere of nitrogen, was added l,4-dibromo-2-methoxybenzene (2.60 g, 9.78 mmol), benzyl piperazine- 1-carboxylate (2.37 g, 10.8 mmol), Pd2(dba)3-CHCij (0.508 g, 0.490 mmol), XantPhos (0,583 g, 0.980 mmol), and NaOtBu (2.82 g, 29.3 mmol) followed by toluene (40 mL). The reaction mixture was stirred, for 3 h at 80 C and then concentrated in vacuo. The resulting crude product was purified by FCC eluting with ethyl acetate/petroleum ether (1 : 10) to afford benzyl 4-(4- (0958) 131 (0959) 144628010 vl bromo-3-methoxyphenyl)piperazine-l-carboxylate as a brown solid (2 g, 50%). LCMS (ESi, m/z): 405, 407 [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 95970-08-4, its application will become more common.

Reference:
Patent; FORMA THERAPEUTICS, INC.; GUERIN, David Joseph; BAIR, Kenneth W.; CARAVELLA, Justin A.; IOANNIDIS, Stephanos; LANCIA JR., David R.; LI, Hongbin; MISCHKE, Steven; NG, Pui Yee; RICHARD, David; SCHILLER, Shawn E. R.; SHELEKHIN, Tatiana; WANG, Zhongguo; (365 pag.)WO2017/139778; (2017); A1;,
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Adding a certain compound to certain chemical reactions, such as: 332-48-9, name is 1-(2-Bromoethoxy)-4-fluorobenzene, 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 332-48-9, Computed Properties of C8H8BrFO

EXAMPLE 49 1-(2-(4-Fluorophenoxy)ethyl)-2-(hydroxymethyl)piperidine hydrobromide From 2-hydroxymethylpiperidine (500 mg, 4.34 mmol) and 2-(4-fluorophenoxy)ethyl bromide (999 mg, 4.56 mmol) there was obtained a colorless oil (970 mg, 88%): 1H NMR (CDCl3) d 1.60-2.11 (m, 6 H), 2.67-3.59 (m, 6 H), 3.80 (dd, J1=11 Hz, J2=3.9 Hz, 1 H), 4.15 (dd, J, =11 Hz, J2=3.9 Hz, 1 H) 4.37-4.42 (m, 2 H), 7.13-7.35 (m, 4 H). The hydrobromide was obtained as a colorless powder (1.08 g, 96%): mp 103.5-105.5 C.; Anal. Calcd for C14H21BrFNO2: C, 50.31; H, 6.33; N, 4.19. Found: C, 50.39; H, 6.15; N, 3.99.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(2-Bromoethoxy)-4-fluorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; Warner-Lambert Co.; Cocensys, Inc.; US6218404; (2001); B1;,
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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. 74137-36-3, name is 1,3-Dibromo-5-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1,3-Dibromo-5-methoxybenzene

Tris [(DIBENZYLIDENEACETONE)] [DIPALLADIUM (0)] (6.53g, 7. [15MMOL)] was added in one portion to a stirred solution of the bromide of Preparation 1 (38. [0G,] [143MMOL),] 1,1′-bis (diphenylphosphino) ferrocene (9.3g, 16. [8MMOL)] and zinc cyanide (20. [OG,] [172MOL)] in N,N-dimethylformamide (300ml) at room temperature under nitrogen. The reaction was heated at [100°C] for 14 hours and cooled to room temperature. Water (1500ml) was added and the mixture was extracted with ethyl acetate (3x500ml). The combined organics were filtered and the filtrate was washed with water (500ml). dried over magnesium sulphate, filtered and concentrated under reduced pressure. The resulting solid was triturated with toluene [(1000ML)] to provide the title compound [(18. 0G)] as a tan solid. [1H-NMR (300MHZ, CDCI3)] : 8 = 3.83 (3H, s), 7.31 (2H, s), 7.48 (1 H, s).

According to the analysis of related databases, 74137-36-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER LIMITED; PFIZER INC.,; WO2004/29042; (2004); 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. 588-96-5, name is p-Bromophenetole belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: p-Bromophenetole

To a solution of 2R-allyl-3S-hydroxy-succinic acid diisopropylester (4.79 g, 18.5 MMOL), 4-bromo PHENETOLE (3.19 MI, 22.2 mmol, 1.2 eq. ) and NEt3 (6.22 ML, 44.6 MMOL, 2.4 eq. ) in CH3CN (40 ml), was added a sonicated (for 2 min) suspension of P (O-TOL) 3 (0.57 g, 2.22 mmol, 0.1 eq. ) and Pd (OAC) 2 (209 mg, 5%) in CH3CN (5 ML). The reaction mixture was heated to reflux for 2 hrs. CH3CN was removed under vacuum. The crude was extracted with AcOEt (3 X 200 ML), washed with water (50 mi) and with brine (50 ML). A purification by flash chromatography afforded the desired 2R- [3- (4-ethoxy-phenyl)-allyl]-3S- hydroxy-succinic acid diisopropyl ester (5.92 g, 84% yield). 1H-NMR ; delta (CDC13), 7.28 (2H, d, J = 8.8Hz), 6.83 (2H, d, J = 8.8Hz), 6.46 (1H, d, J = 15.7Hz), 6.02-6. 12 (1H, m), 4.98-5. 13 (2H, m), 4.26 (1H, dd, J = 7.1, 3. 0HZ), 4.02 (2H, q, J = 7. 0HZ), 3.23 (1H, d, J = 7. 1 HZ), 2.92-2. 97 (1H, m), 2.68-2. 79 (1H, m), 2.49-2. 62 (1H, m), 1.41 (3H, t, J=7.0 Hz) and 1.19- 1.30 (12H, m). LRMS: +ve ion 400 (M+Na).

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

Reference:
Patent; BRITISH BIOTECH PHARMACEUTICALS LTD; LABORATOIRES SERONO S.A.; WO2004/101537; (2004); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

These common heterocyclic compound, 175278-17-8, name is 2-Bromo-4-(trifluoromethoxy)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. category: ethers-buliding-blocks

Intermediate 1: 2-propyl-4-(trifluoromethoxy)aniline A solution of 2-bromo-4-(trifluoromethoxy)aniline (256 mg, 1.00 mmol), [(E)-prop-1-enyl]boronic acid (172 mg, 2.00 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (29.0 mg, 0.0400 mmol), and K2CO3(aq) (1 M, 2 equiv) in MeOH (0.5 mL)/toluene (0.5 mL) was stirred at 125 C. for 4 h. The organic layer was separated, concentrated to dryness, and purified by FCC (SiO2) to give (E)-2-(prop-1-en-1-yl)-4-(trifluoromethoxy)aniline. (E)-2-(Prop-1-en-1-yl)-4-(trifluoromethoxy)aniline and Pd/C (10% on carbon, 30 mg) in MeOH (10 mL) was stirred under H2 (1 atm) for 3 h. After filtration on diatomaceous earth such as Celite, the filtrate was collected and concentrated to dryness to give 2-propyl-4-(trifluoromethoxy)aniline. MS (ESI): mass calcd. for C10H12F3NO, 219.1; m/z found, 220.1 [M+H]+.

The synthetic route of 2-Bromo-4-(trifluoromethoxy)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Janssen Pharmaceutica NV; Bacani, Genesis M.; Chai, Wenying; Edwards, James P.; Smith, Russell C.; Tichenor, Mark S.; Venable, Jennifer D.; Wei, Jianmei; (64 pag.)US2018/289706; (2018); A1;,
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Electric Literature of 446-59-3, 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. 446-59-3, name is 2-Bromo-1-fluoro-3-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows.

Synthesis of 3-Bromo-2-fluoro-4-methoxy-benzaldehyde In a 3-neck 250 mL round bottomed flask equipped with nitrogen lines and a stir bar was placed 2-bromo-1-fluoro-3-methoxy-benzene (2.0 g, 9.75 mmol) and dichloromethane (48 mL). The solution was cooled in an ice water bath for 15 minutes and then titanium tetrachloride (5.02 mL, 45.8 mmol) and dichloromethyl methyl ether (1.32 mL, 14.6 mmol) were added and the reaction mixture was allowed to warm to room temperature and react for 2 hours. The reaction mixture was slowly added to ice water (250 mL) and extracted with dichloromethane (2*100 mL). The organic portions were combined, washed with a saturated sodium bicarbonate solution (75 mL), water (75 mL) and brine (75 mL), dried (MgSO4) and concentrated. The crude material was triturated with hexanes (15 mL) to produce 1.67 g of Int-4 as an off-white solid in 74% yield. MS (ESI+): 233.2 (M+) Int-17Synthesis of 3-Bromo-2-fluoro-4-methoxy-benzaldehyde using titanium(IV)chlorideA solution of 2-bromo-3-fluoroanisol (5.00 g, 24.3 mmol) in dichloromethane (120 mL) was cooled to 0 C. in a salt-ice bath and purged with nitrogen. The reaction was allowed to stir 15 min under nitrogen. To the reaction was added titanium(IV)chloride (23.1 g, 122 mmol), followed by a,a-dichloromethyl-methylether (4.21 g, 36.6 mmol) at 0 C. under nitrogen. The reaction was allowed to warm to room temperature and stirred for 22 h. The red solution was poured into ice water (600 mL), and extracted into dichloromethane (3×200 mL). The organic extracts were combined, washed with saturated aqueous sodium bicarbonate (2×400 mL), water (2×400 mL), and brine (400 mL), dried over sodium sulfate, filtered, and the solvent removed under vacuum to give wet product. The product was dried in a vacuum oven at 80 C. overnight to give Int-17 (5.75 g, quantitative yield).1H NMR (400 MHz CDCl3) delta 10.22 (s, 1H), 7.86 (dd, J=8.8 Hz, 7.6 Hz, 1H), 6.82 (d, J=8.4 Hz, 1H), 4.01 (s, 3H). Synthesis of 3-bromo-2-fluoro-4-methoxy-benzaldehyde (I-30). In a 3-necked 250 mL round-bottomed flask equipped with nitrogen lines and a stir bar was placed 2-bromo-1-fluoro-3-methoxy-benzene (I-29, 2.0 g, 9.75 mmol) and dichloromethane (48 mL). The solution was cooled in an ice water bath for 15 minutes and then titanium tetrachloride (5.02 mL, 45.8 mmol) and dichloromethyl methyl ether (1.32 mL, 14.6 mmol) were added and the reaction mixture was allowed to warm to room temperature and react for 2 hours. The reaction mixture was slowly added to ice water (250 mL) and extracted with dichloromethane (2×100 mL). The organic portions were combined, washed with a saturated sodium bicarbonate solution (75 mL), water (75 mL) and brine (75 mL), dried (MgSO4) and concentrated. The crude material was triturated with hexanes (15 mL) to produce 1.67 g of 3-bromo-2-fluoro-4-methoxy-benzaldehyde (I-30) as an off-white solid in 74% yield. MS (ESI+): 233.2 (M+).

The chemical industry reduces the impact on the environment during synthesis 2-Bromo-1-fluoro-3-methoxybenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; DECODE GENETICS EHF; US2009/136473; (2009); A1;,
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Reference of 934240-59-2, 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 934240-59-2 as follows.

To a mixture of magnesium turnings (12.79g. 533mol), a trace of iodine and 1 ,2-dibromoethane in THF (86.ml)at 70-750C, a solution of (4-bromophenyl (2- fluorophenyl)methyl ether) (100g, 355.6mmol) in THF (216.25ml) was added over about 2 hours. The mixture was heated for a further 2 hours at 70-75C then cooled to room temperature to give a solution of the Grignard reagent. A solution of 1-(1 ,1-dimethylethyl) 2-methyl (2S)-5-oxo-1 ,2-pyrrolidinedicarboxylate (43.25g, 177.8mmol) in THF (216.25ml) was cooled to -600C and the solution of the Grignard reagent was added over 1 hour, then the mixture was stirred for 3 hours at -60C. lsopropanol (43.25ml) was added dropwise, followed by saturated aqueous ammonium chloride (86.5ml) and brine (43.25ml), then the mixture warmed to room temperature. Water (173ml) and 50% acetic acid (50ml) to pH 6- 7, followed by ethyl acetate (129.7ml). The layers were separated and the aqueous extracted with ethyl acetate (2 x 129.7ml). The combined organic layers were washed with brine then concentrated under vacuum. The residue was stirred with hexane (216.2ml), then the solid was filtered and washed with hexane. To the resulting solid, isopropanol (432.5ml) was added and the mixture stirred at 45C for 15 minutes, then cooled to 5- 100C and stirred for 2 hours. The solid was filtered, washed with isopropanol and dried to give the title compound as a solid.1 H NMR (300 MHz, CHCI3-d): delta(ppm): 1.42 (s, 9H); 2.04 (m, 1 H); 2.28 (m, 1 H); 3.03 (m, 2H); 3.74 (s, 3H); 4.37 (m, 1 H); 5.19 (b, 1 H); 5.20 (s, 2H); 7.02 (d, 2H); 7.1 1 (t, 1 H); 7.17 (t, 1 H); 7.33 (m, 1 H); 7.48 (t, 1 H); 7.94 (d, 2H).

According to the analysis of related databases, 934240-59-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/90114; (2008); A1;,
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Ether | (C2H5)2O – PubChem

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. 588-96-5, name is p-Bromophenetole, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 588-96-5

Ethyl 1-(4-ethoxyphenyl)-1H-pyrazole-3-carboxylate (2) A 10 mL Schlenk tube was dried under vacuum, filled with nitrogen and consecutively charged with 19.4 mg (0.102 mmol, 0.2 eq) Cul, 332.3 mg (1.020 mmol, 2.0 eq) Cs2CO3, 100.0 mg (0.714 mmol, 1.4 eq) ethyl 1H-pyrazole-3-carboxylate (6), 102.4 mg (73.0 muL, 0.510 mmol, 1.0 eq) p-bromophenetol and 1 mL dry ACN. The light brown suspension was degassed by vaccum/N2 cycles and stirred first at 82 C. for 7 h and than after adding 0.5 mL dry DMF (solubility issue) at 120 C. for further 65 h. The GC-MS analysis showed full conversion. ACN and DMF were removed under high pressure and the brown residue was suspended in 10 mL EtOAc. After filtration of the brown suspension through a pad of silica and flushing with 150 mL EtOAc the colorless filtrate was concentrated under reduced pressure leading to 52.1 mg (39%) crude product as a green-brown oil. Final purification by column chromatography (CH/EtOAc 3:1, size: 15.5*2.0 cm, 20 g silica gel) yielded the pure title compound. yield: 10.2 mg (8%); orange solid; M.p.: 88-90 C.; Rf (CH/EtOAc 3:1): 0.40; 1H-NMR (300 MHz, DMSO-d6): delta (ppm)=8.51 (d, 4J=2.4 Hz, 1H, Ar-H), 7.78 (d, 3J=9.0 Hz, 2H, Ar-H), 7.07 (d, 3J=9.0 Hz, 2H, Ar-H), 6.97 (d, 4J=2.4 Hz, 1H, Ar-H), 4.31 (q, 3J=6.9 Hz, 2H, CH2), 4.08 (q, 3J=7.2 Hz, 2H, CH2), 1.37-1.29 (m, 6H, 2 CH3); 13C-NMR (75.5 MHz, DMSO-d6): delta (ppm)=161.4 (C=O), 157.6 (Cq), 143.6 (Cq), 132.5 (Cq), 129.5 (CHAr), 120.7 (2CHAr), 115.0 (2CHAr), 119.8 (CHAr), 63.4 (CH2), 60.3 (CH2), 14.5 (CH3), 14.1 (CH3); GC-MS (NM-50_S2): tR=7.722 min (m/z=260.1, 98.0% M+, BP).

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 588-96-5.

Reference:
Patent; Technische Universitaet Graz; Karl-Franzens-Universitaet Graz; Schweiger, Martina; Romauch, Matthias; Zimmermann, Robert; Mayer, Nicole; Breinbauer, Rolf; US9206115; (2015); B2;,
Ether – Wikipedia,
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