Tag: M.W=200-300

Application of 89794-02-5,Some common heterocyclic compound, 89794-02-5, name is 4-Bromo-2-chlorotoluene, molecular formula is C7H6BrCl, 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 aryl bromide (3 equiv), Mg (3 equiv), and DIPAB or DICAB (1 equiv) in dry THF (1 mL/mmol) was added at r.t. a solution of 2 M PhMgBr in THF (0.05 equiv). After 10 min (or at the end of gas evolution on large scale), the mixture was heated to 70 C until no aryl bromide remained in the mixture (8-16 h). At 0 C, dry MeOH (1mL/mmol) was added (caution, exothermic reaction). After 1 h, the mixture was concentrated under reduced pressure, and diluted in a mixture of 1 M HCl/MeOH (7:3, 10 mL/mmol), after 1 h, the product was extracted with Et2O (3 ¡Á 10 mL/mmol) and the combined organic phases were washed with 1 M HCl (10 mL/mmol) and brine (3 ¡Á 10mL/mmol). Organic phases were then dried (anhyd Na2SO4), and concentrated under reduced pressure. The residue was dissolved in Et2O (4 mL/mmol) and ethanolamine (1.2 equiv) was added. Depending on the substituents, precipitation occurs spontaneously or requires the addition of pentane. Crystals were filtered, washed with pentane and dried under vacuum to yield the pure 2-aminoethyl borinate.

The synthetic route of 89794-02-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Richard, Jimmy; Birepinte, Melodie; Charbonnier, Jean Baptiste; Liautard, Virginie; Pinet, Sandra; Pucheault, Mathieu; Synthesis; vol. 49; 4; (2017); p. 736 – 744;,
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Electric Literature of 766545-20-4, 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. 766545-20-4 name is 2-Chloro-5,6,7,8-tetrahydro-1,6-naphthyridine hydrochloride, 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.

To a stirred solution of cyclopropylacetic acid (24 mg, 0.24 mmol) in DMF (1 ml) at room temperature was added HBTU (185 mg, 0.49 mmol) and HOBt (72 mg, 0.53 mmol) sequentially and the resulting solution stirred for 15 mins. 2-Chloro-5,6,7,8-tetrahydro-l,6- naphthyridine hydrochloride (50 mg, 0.24 mmol) and DIPEA (89 mul, 0.53 mmol) in DMF (ImI) were then added and the resulting mixture stirred at room temperature for 16 hours. The reaction mixture was evaporated to dryness and the residue was purified by FCC on silica gel (99: 1 : 1 DCM/MeOH/NH3) to provide the title compound (56 mg, 95%).LCMS data: Calculated MH+ (251); Found 89% (MH+) m/z 251, Rt = 1.14 mins. NMR data: 1H NMR (250 MHz, CDCl3) delta ppm 7.44 (1 H, d, J=7.5Hz), 7.20 (1 H, d, J=7.5Hz), 4.76 (2 H, s), 3.78 (2 H, t, J=7.5Hz), 3.00 – 3.06 (2 H, m), 2.40 (2 H , d, J=7.5Hz), 1.03 – 1.16 (1 H, m), 0.56 – 0.64 (2 H, m), 0.16 – 0.25 (2 H, m).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-5,6,7,8-tetrahydro-1,6-naphthyridine hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; EVOTEC NEUROSCIENCES GMBH; WO2009/135842; (2009); 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. 57310-39-1, name is 3-Bromo-4-chlorotoluene, A new synthetic method of this compound is introduced below., Formula: C7H6BrCl

A solution of 2-bromo- l -chloro-4-methylbenzene (24 g, 0. 1 17 mo l, l eq) in cone. H2S04 (200 mL) was cooled to 0-5C. Nitric acid (5 mL, 1.48g/ml, 0.1 17mol) in cone. H2S04 ( 13 ml) was added dropwise to the mixture slowly. After the addition was completed, the reaction was stirred at 0 C for 3h. The reaction mixture was poured into 200g ice-water and extracted with DCM (2×100 mL). The combined organic layers were washed with water , dried over Na2S04, and concentrated to afford crude 166, which was recrystallized from ethanol (200ml) to afford 166 as a pale yellow solid (24 g, 83%). ? NM (400 MHz, CDCb) ppm: 8.08 (s, 1H), 7.63 (s, 1 H), 2.56 (s, 3H).

The synthetic route of 57310-39-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AFRAXIS, INC.; CAMPBELL, David; DURON, Sergio, G.; WO2013/43232; (2013); A2;,
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14862-52-3, name is 3,5-Dibromochlorobenzene, belongs to chlorides-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. Safety of 3,5-Dibromochlorobenzene

General procedure: To degassed DMF (8.0 mL) was added Pd(dppf)Cl2 (73 mg, 0.10 mmol), bis(pinacolato)diboron (508 mg, 2.0 mmol), potassium acetate (589 mg, 6.0 mmol), and 2,6-dibromobenzene (0.121 mL, 236 mg, 1.0 mmol) in order at room temperature. The mixture was heated to 130 C for 1 hour to complete formation of the boronic ester. Then 3-bromopyridine (0.289 mL, 474 mg, 3.0 mmol) and degassed aqueous sodium hydroxide (2.00 mL, 3.0 M, 6.0 mmol) were sequentially added to the hot reaction, and heating at 130 C was continued for another 3 hours when the reaction was complete (by GCMS). The reaction was cooled and evaporated to a residue in vacuo. The residue was extracted with chloroform, and the combined extracts were concentrated and applied to preparative silica TLC plates. After development by 1:1 THF:EtOAc the product bands were removed and extracted with DME. Evaporation of extract solutions resulted in the yields. The products could be purified by sublimation at 180 C and 10 mmHg if needed.

The synthetic route of 14862-52-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Avitia, Bertoldo; MacIntosh, Eric; Muhia, Samuel; Kelson, Eric; Tetrahedron Letters; vol. 52; 14; (2011); p. 1631 – 1634;,
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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. 50594-82-6, name is 3,4,5-Trichlorobenzotrifluoride, This compound has unique chemical properties. The synthetic route is as follows., name: 3,4,5-Trichlorobenzotrifluoride

Example 1 : Preparation of a mixture comprising 1 ,3-dichloro-2-fluoro-5- trifluoromethylbenzene of the formula Il and 1 ,2-dichloro-3-fluoro-5- trifluoromethylbenzene of the formula III; 23 g (0.396 mol) KF, 12.8 g (0.03 mol) PPh4Br, 91.2 g sulfolane and 152 ml toluene were mixed in a 500 ml reactor. Toluene was distilled off under reduced pressure(1400C, thetaOmbar; aceotropic removal of water). After cooling to 1000C, 76 g (0.305 mol) 1 ,2,3-trichloro-5-trifluoromethylbenzene were added and the resulting mixture was heated at 190C for 15 h under reduced pressure (100 mbar). The mixture of 1 ,3- dichloro-2-fluoro-5-trifluoromethylbenzene and 1 ,2-dichloro-3-fluoro-5- trifluoromethylbenzene was distilled off simultaneously via a column. Two distillation fractions were obtained, which contained 31 % GC area-% of the product mixture, 1 % GC area-% of difluoro compounds and 6.6% GC area-% of the educt 1 ,2,3-trichloro-5- trifluoromethylbenzene. The identity of the mixture was determined by GC/MS spectrometry and 19F-NMR spectroscopy.

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 50594-82-6.

Reference:
Patent; BASF SE; WO2008/113660; (2008); A1;,
Chloride – Wikipedia,
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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. 19752-55-7, name is 1-Bromo-3,5-dichlorobenzene, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 1-Bromo-3,5-dichlorobenzene

A 250 ml round-bottom flask was charged with magnesium (turnings; 2.68 g; 110 mmol), and argonated. Then, Et2O(60 ml), I2 (one crystal) were added, and a solution of 1-bromo-3,5-dichlorobenzene (25.32 g; 112.1 mmol) in Et2O (80 ml) was added portionwise over 45 min with stirring. After 2 h the mixture was cooled with ice-water bath and AsCl3 (2.8 ml; 33.4mmol) was added dropwise, that caused formation of crystalline precipitate. Stirring was continued at RT for 16 h, and aqueous NH4Cl (100 ml; 10percent) was added. The resulted mixture was extracted with ethyl acetate (3 100 ml), and combined organic phases were washed with brine (100 ml), and dried over MgSO4. The mixture was filtered, evaporated, and residue viscous orange oil was crystallized from n-hexane (dissolved in boiling solvent and slowly cooled to ca. 0 ¡ãC) in three crops(first crop 30 ml; second crop 11 ml; third crop 4 ml) to obtain 8c (14.01 g; 27.31 mmol; 82percent) as a white solid.

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 19752-55-7.

Reference:
Article; Grudzie?, Krzysztof; Basak, Tymoteusz; Barbasiewicz, Micha?; Wojciechowski, Tomasz M.; Fedory?ski, Micha?; Journal of Fluorine Chemistry; vol. 197; (2017); p. 106 – 110;,
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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. 19752-55-7, name is 1-Bromo-3,5-dichlorobenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 1-Bromo-3,5-dichlorobenzene

(l-Benzyl-lH-[l,2,4]triazol-3-yl)-(3,5-dichloro-phenyl)-amine (Compound 23) A mixture ofl-benzyl-lH-l,2,4-triazol-5-amine 2,2,2-trifluoroacetate (mixture of isomers) (292 mg, 1.01 mmol, Eq: 1.24),l-bromo-3,5-dichlorobenzene (185 mg, 819 muiotaetaomicron, Eq: 1.00), sodium tert-butoxide (341 mg, 3.55 mmol, Eq: 4.33), tris(dibenzylideneacetone)dipalladium(0) (18.7 mg, 20.5 muiotaetaomicron, eq: 0.025) and 2-di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl (34.8 mg, 81.9 muiotaetaomicron, Eq: 0.10) in a 2-5 mL microwave vessel. Sealed the vessel. Evacuated the system and recharged with nitrogen (2x). Added toluene and heated in an oil bath at 110¡ãC overnight. The reaction mixture was diluted with EtOAc, washed with water and brine. Dried (Na2S04) and concentrated over celite. The crude material was purified by flash chromatography (silica gel, SF40-80 g, 25percent to 50percent EtOAc in hexanes) to give 2 major products. The more polar fraction was desired product 116 mg, which was triturated with methanol, filtered and rinsed with ether to give 42 mg (16percent) of desired product as a white solid. The less polar fraction was determined to be isomeric product, (2-Benzyl-2H-[l,2,4]triazol-3-yl)-(3,5-dichloro-phenyl)- amine. MS m/z 319 [M+H]

The synthetic route of 19752-55-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; DING, Qingjie; JIANG, Nan; WEIKERT, Robert James; WO2014/135472; (2014); A1;,
Chloride – Wikipedia,
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14490-19-8, name is 1,4-Dichloropyrido[3,4-d]pyridazine, belongs to chlorides-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. Product Details of 14490-19-8

To l,4-dichloropyrido[3,4-d]pyridazine 3 (4.80 g, 24.0 mmol) and Hnig’sBase (14.7 ml, 84.0 mmol) in NMP (10 ml) was added (2R,5S)-2,5-dimethylpiperazine (4.1 1 g, 36.0 mmol). The reaction was stirred at 100C. After 2 h, the reaction contents were poured into saturated sodium bicarbonate (10x volume) and extracted with dichloromethane (4 x 50 mL). Silica gel chromatography (gradient 0 to 2.5% MeOH in 30% EtOAc in CH2Cl2 with 2.5% TEA additive) provided 1.4 g of l-chloro-4-(rac-2,5-trans-dimethylpiperazin-l-yl)pyrido[3,4- d]pyridazine 43. 1H NMR (500 MHz, CDC13) delta ppm 9.66 (s, 1 H) 9.08 (d, J=5.6 Hz, 1 H) 7.97 (d, J=5.6 Hz, 1 H) 3.77 (tdd, J=I 1.8, 5.9, 3.4 Hz, 1 H) 3.43 (dd, J=12.1, 2.6 Hz, 1 H) 3.17 – 3.32 (m, 2 H) 2.91 (dd, J= 10.5, 2.0 Hz, 1 H) 2.74 (dd, J=I 1.7, 10.3 Hz, 1 H) 1.13 (d, J=6.1 Hz, 3 H) 1.12 (d, J=6.6 Hz, 3 H).

The synthetic route of 14490-19-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; WO2009/35568; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 933190-51-3, 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. 933190-51-3, name is 8-Bromo-6-chloroimidazo[1,2-b]pyridazine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 1. Preparation of (6-Chloro-imidazo[1,2-b]pyridazin-8-yl)-[5-(4-isopropyl-piperazin-1-yl)-pyridin-2-yl]-amine A mixture of 8-bromo-6-chloroimidazo[1,2-b]pyridazine (200 mg, 862 mumol, Eq: 0.95) and 5-(4-isopropylpiperazin-1-yl)pyridin-2-amine (200 mg, 908 mumol, Eq: 1.00) in DMF (10.0 ml) was cooled to 0 C. To this reaction mixture was added sodium hydride (116 mg, (60% in mineral oil), 2.9 mmol, Eq: 3.2). The reaction was allowed to stir at 0 C. for 10 min then allowed to warm to room temperature and stir 18 h. The reaction mixture was quenched with sat. NaHCO3 (aq) and diluted with water and EtOAc. The organic layer was separated and the aqueous phase was extracted with EtOAc. The organic layers were combined, dried over MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 0% to 20% (60:10:1 DCM:MeOH:NH4OH)/DCM gradient) to give a residue that was placed under high vacuum for 18 h to afford (6-chloro-imidazo[1,2-b]pyridazin-8-yl)-[5-(4-isopropyl-piperazin-1-yl)-pyridin-2-yl]-amine (78 mg, 23%). LC/MS-ESI observed [M+H]+ 372.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 8-Bromo-6-chloroimidazo[1,2-b]pyridazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hoffmann-La Roche Inc.; Brotherton-Pleiss, Christine E.; Lopez-Tapia, Francisco Javier; Lou, Yan; US2013/150360; (2013); A1;,
Chloride – Wikipedia,
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Electric Literature of 19752-55-7,Some common heterocyclic compound, 19752-55-7, name is 1-Bromo-3,5-dichlorobenzene, molecular formula is C6H3BrCl2, 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 3,5-dichlorobromobenzene (225 mg, 1 mmol), 4-hydroxypiperidine (101 mg, 1 mmol), BINAP (31.2 mg, 0.05 mmol), and NaOtBu (114 mg, 1.2 mmol) in toluene (3 mL) under argon, was added Pd(OAc)2 (8 mg, 0.03 mmol). The resulting reaction mixture was stirred at 100oC for 4 h. The flask was cooled to room temperature and then partitioned between ethyl acetate (20 mL) and water (20 mL). The organic layer was separated, washed with brine, and dried over Na2SO4. After evaporation of the volatiles, the residue was subjected to column chromatography, eluting with hexane/ethyl acetate (4/1) to afford 1-(3,5-dichlorophenyl)piperidin-4-ol as a colorless oil (210 mg, 85percent) as well as a small amount of 1-(3,5-dichlorophenyl)piperidin-4-one (10 mg, 5percent). A mixture of the above product (210 mg, 0.85 mmol) and Dess-Martin periodinane (424 mg, 1 mmol) were dissolved in DCM (4 mL) and stirred for 1 h at room temperature. After evaporation of the volatiles, the residue was subjected to column chromatography, eluting with hexane/ethyl acetate (15/1) to afford 1 as a colorless oil (169 mg, 77percent). 1H NMR (500 MHz, CDCl3) delta 6.82 (d, J = 2.0 Hz, 1H), 6.78 (d, J = 1.5 Hz, 2H), 3.61 (t, J = 6.0Hz, 4H), 2.55 (t, J = 6.0 Hz, 4H); 13C NMR (125 MHz, CDCl3) delta 207.3, 150.7, 136.0X2, 119.1, 113.5X2, 47.7, 40.5; MS (ESI): m/z 244.0 [M+H]+.

The synthetic route of 19752-55-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Yinan; Silverman, Richard B.; Tetrahedron Letters; vol. 54; 6; (2013); p. 573 – 575;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics