Tag: M.W=100-200

These common heterocyclic compound, 3970-51-2, name is 5-Chloro-1H-indene, 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. COA of Formula: C9H7Cl

General procedure: A solution of 5-methoxy-1H-indene (2.40 g, 16.4 mmol) in MeOH (20mL) and CH2Cl2 (50 mL) was cooled to -78 C under N2. O3 (with O2 carrier gas) was bubbled through the solution for 30 min. An exotherm to -65 C occurred while the reaction was in progress; this subsided at the end of the reaction and a blue colouration of dissolved ozone was seen. Unreacted ozone was removed by flushing the reaction vessel with N2. NaHCO3 (1.75 g, 20.9 mmol) and Me2S (3.28 mL,44.3 mmol) were added. The cooling bath was removed and the mixture was stirred for 16 h at r.t.. Concd (28-30%) aq ammonia (20 mL)was added and the mixture stirred for a further 24 h. The mixture was extracted with CH2Cl2 (3 × 100 mL) and the combined organic phases were extracted with 5% aq HCl (2 × 100 mL). The combined aqueous phases were washed with CH2Cl2 (100 mL) and basified with Na2CO3 to pH 10 with stirring. An oil precipitated from solution; the mixture was extracted with CH2Cl2 (2 × 100 mL). The combined organic extractswere washed with sat. brine (50 mL), dried (MgSO4) and evaporated to afford the title compound 6 (1.27 g, 49%) as a brown oil,which was used without further purification.

The synthetic route of 5-Chloro-1H-indene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Pearson, Stuart E.; Fillery, Shaun M.; Goldberg, Kristin; Demeritt, Julie E.; Eden, Jonathan; Finlayson, Jonathan; Patel, Anil; Synthesis; vol. 50; 24; (2018); p. 4963 – 4981;,
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Synthetic Route of 29242-84-0, These common heterocyclic compound, 29242-84-0, name is 2-Chloro-4-methoxyaniline, 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.

Part H. A solution of the aniline from Part G (7.98 g, 50 mmol) in conc. HCl (25 mL) was cooled to -5 C., and treated dropwise with a concentrated aqueous solution of sodium nitrite (3.80 g, 55.1 mmol). After 30 minutes, the mixture was charged with 15 mL cyclohexane and 15 mL dichloromethane, then treated dropwise with a concentrated aqueous solution of potassium iodide (16.6 g, 100 mmol). This mixture was allowed to stir for 4 hours, then was extracted with dichloromethane (2*100 mL). The extracts were washed in sequence with 1 N aqueous sodium bisulfite (100 mL) and brine (60 mL), then combined, dried over magnesium sulfate, filtered and evaporated to afford sufficiently pure product, 3-chloro-4-iodoanisole (7.00 g, 26.1 mmol, 52%). TLC RF 0.39 (5:95 ethyl acetate-hexane). 1 H NMR (300 MHz, CDCl3): d 7.69 (1H, d, J=8.8 Hz), 7.03 (1H, d, J=3.0 Hz), 6.57 (1H, dd, J=8.8, 3.0 Hz), 3.78 (3H, s). MS(H2 O-GC/MS): m/e 269 (100).

Statistics shows that 2-Chloro-4-methoxyaniline is playing an increasingly important role. we look forward to future research findings about 29242-84-0.

Reference:
Patent; Dupont Pharmaceuticals Company; US6143743; (2000); A;,
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Reference of 41332-02-9,Some common heterocyclic compound, 41332-02-9, name is 1-(2-Chloroethyl)naphthalene, molecular formula is C12H11Cl, 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 borosilicate glass tube (OD 0.6 mm, length 12 cm) was packed with PS-supported P2tBu (150 muiotatauiotaomicron base, loading 1.6 mmol/g, 93.75 mg) mixed with glass beads (212-300 mutaueta, 100-500 mg) and placed in a column oven in a LabView controlled automation apparatus. 18F- trapping: 18F- (target water, 3.5 mL, 500-5000 MBq) passed through the column at room temperature (flow 1.5 mL/min) . MeCN (dry, 4 ml, flow 2 mL/min) was passed through the column at room temperature followed by a helium gas flush through the column until excess of solvent was removed. Radiofluorination : Radiofluorination solvent (MeCN for mannose triflate, MeCN/tBuOH 1:5 for FLT-ONs, toluene for the naphthalene analogues and 2-nitro-3-methoxypyridine, dry, 4 mL, flow 2 mL/min) was passed through the column at room temperature followed by the substrate (50-100 muiotatauiotaomicron) dissolved in radiofluorination solvent (dry, 3 mL) and passed through the column at 120C (flow 0.55 mL/min) . Radiofluorination solvent (dry, 2 mL, flow 0.55 mL/min) was then passed through the column to elute the remaining product. The fluorinated product wasanalyzed by radio-TLC (eluent heptane : EtOAc 80:20 for the naphthalene analogues, MeCN:H20 95:5 for hydrolyzed FDG, DCM : MeOH 9:1 for hydrolyzed FLT, petroleum ether :EtOAc for the pyridine analogue).

The synthetic route of 41332-02-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TECHNICAL UNIVERSITY OF DENMARK; ZHURAVLEV, Fedor; MATHIESSEN, Bente; WO2014/20035; (2014); A1;,
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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. 2039-83-0, name is 3,4-Dichlorostyrene, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 2039-83-0

General procedure: To a solution of FeCl3 6 H2O (6.8 mg, 25.0 mumol, 5 mol%) in 9 mL 2-Me-2-BuOH, an imidazole basedligand (50.0 mumol, 10 mol%) was added at room temperature under air. After addition of the olefin (500mumol), H2O2 (30 wt% in H2O, 170 muL, 1.50 mmol) mixed with 830 muL 2-Me-2-BuOH was added via syringepump over a 1 h period. The reaction was quenched with 50 muL saturated aqueous Na2SO3 solution. Afterextraction with CH2Cl2, the organic phases were combined and evaporated to dryness. The crude mixture was filtered through a SiO2-plug (1 cm, eluted with CH2Cl2). In order to determine the yield via 1H-NMR,pyrazine was added in a defined amount as an internal standard. Afterwards, purification was carriedout by means a preparative TLC plate (hexane/ethyl acetate) for the HPLC sample preparation in orderto determine enantioselectivity.

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 2039-83-0.

Reference:
Article; Fingerhut, Anja; Vargas-Caporali, Jorge; Leyva-Ramirez, Marco Antonio; Juaristi, Eusebio; Tsogoeva, Svetlana B.; Molecules; vol. 24; 17; (2019);,
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Related Products of 21745-41-5, 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. 21745-41-5, name is 1,2-Diamino-3-chlorobenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Compound 60a:; Chiral To a 5.5 N HCI solution (9 mL) of 1 ,2-diamino-3-chloro-benzene (1.3 g, 9.12 mmol) was added H-D- Asp-OH (3.6 g, 27.4 mmol). The mixture was refluxed for 72h. It was filtered after cooling down to EPO room temperature. The filtrate was purified by prep. HPLC to give the title compound in 41% yield (0.9g). 1H NMR (DMSO-d6): delta 7.52 (1 H, dd, J=8.1 , 1 Hz), 7.28 (1 H, dd, J=7.8, 1 Hz), 7.20 (1 H, t, J=7.8Hz), 4.54 (1 H, t, J=6.8Hz), 3.49 (1 H, dd, J=16.4, 5.8Hz), 3.39 (1 H, dd, J=16.2, 7.1 Hz). LCMS (APCI): 240 (M+H+).

The synthetic route of 1,2-Diamino-3-chlorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER, INC.; WO2006/40646; (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. 90390-33-3, name is 3-Chloro-5-fluorobenzylamine, A new synthetic method of this compound is introduced below., Formula: C7H7ClFN

A solution of ethyl 2-oxopyrrolidine-3-carboxylate (180.00 g, 929.61 mmol) and (3-chloro-5-fluoro-phenyl) methanamine (148.36 g, 929.61 mmol) in xylene (4.00 L) is heated to 130 for 16 hours. The reaction mixture is cooled to 10 and a solid precipitates after 30 minutes. The suspension is filtered and the filter cake is washed with xylene (3×500 mL) , petroleum ether (2×500 mL) and dried in vacuum to give the title product (81 g) . The filtrates are concentrated under reduced pressure and the residue in xylene (3 L) is heated to 130 for 40 hours. The reaction mixture is cooled to 10 and solid precipitates after 30 minutes. The suspension is filtered and the filter cake is washed with xylene (2×500 mL) , petroleum ether (2×500 mL) , and dried in vacuum to give the title product (81.38 g) . The combined product (164.38 g, 607.26 mmol, 65.32) is obtained as a white solid. ES/MS m/z 270.9 (M+H) .

The synthetic route of 90390-33-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; LILLY CHINA RESEARCH AND DEVELOPMENT CO., LTD.; HO, Koc Kan; QUAN, Weiguo; ZHOU, Jingye; (38 pag.)WO2017/5069; (2017); A1;,
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Application of 69411-05-8,Some common heterocyclic compound, 69411-05-8, name is 3-Chloro-5-trifluoromethylaniline, molecular formula is C7H5ClF3N, 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 solution of 3-chloroaniline 5a (37mg, 0.33mmol) in H2O (10mL cooled to-5C) was added 0.2mL of 2N HCl (aq.). To the resulting acidic aniline solution, 1N solution of sodium nitrite (0.33mL, 0.33mmol) was added dropwise to generate the aryldiazonium salt solution 6a. To the aryldiazonium salt solution was added sodium acetate (54mg, 0.66mmol), followed by 1mL solution of crude 3-oxo-3-(3-phenylisoxazol-5-yl)propanenitrile 4a (88mg, 0.33mmol) in ethanol. The reaction mixture was stirred at 0C for 5min, and then poured onto H2O (10mL) and extracted with ethyl acetate (20mL). The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by short column chromatography on silica gel, eluting with hexane/ethyl acetate (2/1) to provide the desired product 7 (67mg, 50% for two steps from 3a) as a yellow solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Chloro-5-trifluoromethylaniline, its application will become more common.

Reference:
Article; Ye, Na; Zhu, Yingmin; Liu, Zhiqing; Mei, Fang C.; Chen, Haiying; Wang, Pingyuan; Cheng, Xiaodong; Zhou, Jia; European Journal of Medicinal Chemistry; vol. 134; (2017); p. 62 – 71;,
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Electric Literature of 67330-62-5, 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 67330-62-5 as follows.

Example 4Synthesis of M-MIPACDEAIn a 5 litre flanged reaction vessel were placed a mixture of 137 ml of sulphuric acid, 580 ml water and 313 ml propan-2-ol. To this were added 250 grams of 3-chloro-2,6-diethylaniline and 203 grams of 2-methyl-6-isopropylaniline. The flask was provided with a stirrer, dropping funnel and condenser and the temperature was raised to 60 C.Formalin solution (35% w/w), 120 ml, was added over a period of 1 hour and heating was subsequently continued for 5 hours. The vessel contents were cooled and neutralised with ammonia solution.The product was extracted into ethyl acetate, washed with water, dried over sodium sulphate, filtered and rotary evaporated to give 467 grams of an amber liquid.Analysis by HPLC showed that the desired hybrid methylene bis-aniline M-MIPACDEA is present at 63% of the total, together with 15% of M-MIPA and 21% of M-CDEA.The liquid showed no sign of crystallisation over 3 months.

According to the analysis of related databases, 67330-62-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; HEXCEL COMPOSITES LIMITED; US2012/316262; (2012); 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. 17601-75-1, name is 2,4-Dichloro-5-methylaniline, A new synthetic method of this compound is introduced below., Quality Control of 2,4-Dichloro-5-methylaniline

Comparative Example 2-11-(2′,2′,2′-Trichloroethyl)-2,4-dichloro-5-methylbenzene; At room temperature, 7.04 g [0.04 mol] of 2,4-dichloro-5-methylaniline are introduced into 28 ml of conc. hydrochloric acid, the mixture is cooled to -5 to 0 C. and a solution, cooled to 0 C., of 3.31 g [0.048 mol] of NaNO2 in 80 ml of water is added dropwise within 60 minutes. Subsequently, the mixture is stirred at -5 to 0 C. for 15 minutes. Subsequently, 3.23 g [0.024 mol] of copper(II) chloride are added. To this mixture is added dropwise, at 0 C. within 30 minutes, a solution of 38.8 g [0.4 mol=10 molar equivalents] of vinylidene chloride in 130 ml of acetone. The mixture is allowed to come to room temperature with good stirring and left to react for another 3 hours. The reaction mixture is diluted with 100 ml of water and extracted twice with 70 ml each time of MTBE. The combined organic phases are washed with 30 ml of water, dried over sodium sulphate and concentrated under reduced pressure. This gives 12.3 g of oil which, according to GC-MS, contains 64.05 area % of 1-(2′,2′,2′-trichloroethyl)-2,4-dichloro-5-methylbenzene. This corresponds to a yield of 67.4% of theory.The GC-MS shows, as by-products, 5.7 area % of Sandmeyer product and 23.8 area % of 1,5-dichloro-2-methyl-4-(2′,2′,4′,4′,4′-pentachlorobutyl)benzene.

The synthetic route of 17601-75-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer CropScience AG; US2010/234651; (2010); A1;,
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Electric Literature of 2770-01-6, 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. 2770-01-6, name is 4-Chloro-1H-imidazo[4,5-c]pyridine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

The chiral cyclopentenyl moiety 5 (below) was prepared from D-ribose in 8 steps following a previously reported synthetic method via a chiral induction, a regioselective protection of hydroxy group and ring-closing metathesis with 0.1 mole% of the 2nd generation Grubbs catalyst as key steps. 10; The other key intermediate 7 was synthesized according to the previously reported procedure11 from commercially available 4-amino-2-chloropyridine (6) in 4 steps (overall 54% yield) as shown in Scheme 1. Mitsunobu reaction of 7 with 5 provided a mixture of the N9- and N7-regioisomers (8:9 = 2:1) in 94% yield. The separation of the desired product (8) from the reaction mixture was difficult by silica gel column [isolated yields: 20% (8) and 20% (9), respectively]. The ratio of the two isomers was determined by 1H-NMR, and their configuration was identified by Nuclear Overhouser Effect (ID-NOE), which indicated the interaction between the C1 ‘-H and the aromatic C3-H of compound 8, whereas the same effect was not present in compound 9.

The synthetic route of 4-Chloro-1H-imidazo[4,5-c]pyridine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY OF GEORGIA RESEARCH FOUNDATION, INC.; WO2007/47793; (2007); A2;,
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