Tag: M.W=200-300

Electric Literature of 116557-46-1,Some common heterocyclic compound, 116557-46-1, name is 3-Bromo-2-methoxyaniline, molecular formula is C7H8BrNO, 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.

In the flask will come from step 23-bromo-2-methoxyaniline (1.94 g, 9.60 mmol)4,4,4 ‘, 4’, 5,5,5 ‘, 5′-octamethyl-2,2’-bis(1,3,2-dioxaborolane)(3.66 g, 14.40 mmol),PdCl2 (dppf) -CH2Cl2 (0.392 g, 0.480 mmol) and potassium acetate (2.83 g, 28.8 mmol) in dioxane (32 mL)The solution was heated to reflux (about 100 & lt; 0 & gt; C) overnight,Then cooled to room temperature,Concentrated on diatomaceous earth in a vacuum.The crude product was purified by flash chromatography using 120 g of a silica gel column (solid loading) with 0-50% ethyl acetate / hexane. The appropriate fractions were collected (eluted with nearly 25% EtOAc / hexanes) and concentrated in vacuo,To give 2-methoxy-3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) aniline in an off-white crystalline solid form (1.47 g , 5.78 mmol, 60.2% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Bromo-2-methoxyaniline, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; MOSLIN,, RYAN M.; WEINSTEIN,, DAVID S.; WROBLESKI,, STEPHEN T.; ZHANG,, YANLEI; TOKARSKI,, JOHN S.; MERTZMAN,, MICHAEL E.; LIU,, CHUNJIAN; (124 pag.)TWI582077; (2017); B;,
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Electric Literature of 170015-99-3, 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. 170015-99-3, name is 2-(4-(Trifluoromethoxy)phenyl)ethanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Under nitrogen atmosphere, ethanol (30 mL), immediate III (3 mmol) and titanium (IV) isopropoxide (9 mmol) were added to a three-necked round bottom flask and stirred for 0.5 h, then the substituted ethylamine (3 mmol) was dropped into the solution and stirred for 3 h at room temperature. Subsequently, sodium borohydride (4.5 mmol) was added to the flask slowly, the reductive amination reaction was maintained for 3 h. According to the TLC monitoring results, the ammonia water (2 mol L-1, 10 mL) was poured into the flask to quench the reaction. The resulting mixture was filtered in vacuum and evaporated on rota vapor (Buchi). Hereafter, dissolved the residue with ethyl acetate (50 mL), and the solution was washed with 2 mol L-1 hydrochloric acid (30 mL), saturated aq NaHCO3 solution (30 mL), and brine (40 mL), successively, dried over anhydrous Na2SO4 and filtered. Solvent was evaporated in vacuum, and the residue was purified by silica gel column chromatography (petroleum ether / ethyl acetate as eluents). Finally, the samples were recrystallized from ethyl acetate / petroleum ether to afford target compounds with higher purity.

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, 2-(4-(Trifluoromethoxy)phenyl)ethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Cai, Nan; Cui, Zining; Feng, Zhihui; He, Lu; Ji, Mingshan; Li, Xinghai; Qi, Zhiqiu; Qin, Peiwen; Wang, Kai; Bioorganic and medicinal chemistry letters; (2019);,
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Some common heterocyclic compound, 20469-65-2, name is 1-Bromo-3,5-dimethoxybenzene, molecular formula is C8H9BrO2, 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

General procedure: General procedure for the preparation of arylalkynes 2a-q (non-decarboxylative approach, method A). An oven-dried 20 mL Schlenk tube equipped with a magnetic stirring bar and a rubber septum was charged with Pd(OAc)2 (6.7 mg, 30 mumol), tri(p-tolyl)phosphine (18.2 mg, 60 mumol). After purging the vessel with alternating vacuum and nitrogen cycles, degassed THF (3 mL), 1,8-diazabicycloundec-7-ene (450 muL, 3.0 mmol), 2-methylbut-3-yn-2-ol (120 muL, 1.24 mmol) and aryl bromides 1a-q (1.0 mmol) were added via a syringe (solid aryl bromides were added as solution in degassed THF) and the mixture was stirred at 80 C for 6 h. After cooling to rt the mixture was diluted with water (20 mL) and extracted with AcOEt (3 20 mL). Combined organic extracts were washed with H2O (20 mL), saturated aqueous NaCl (20 mL), dried over MgSO4 and concentrated in vacuum. The crude product was purified by silica gel chromatography (eluant hexane/Et2O gradient) affording the corresponding products 2a-q.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 20469-65-2, its application will become more common.

Reference:
Article; Caporale, Andrea; Tartaggia, Stefano; Castellin, Andrea; De Lucchi, Ottorino; Beilstein Journal of Organic Chemistry; vol. 10; (2014); p. 384 – 393;,
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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. 5111-65-9, name is 2-Bromo-6-methoxynaphthalene, A new synthetic method of this compound is introduced below., Recommanded Product: 2-Bromo-6-methoxynaphthalene

Under argon atmosphere, 2.37 g (0.01 mol) of 2-bromo-6-methoxynaphthalene and 40.578 g of Pd (PPh3)(0.5 mmol) of CuI, 0.095 g (0.5 mmol) of CuI and 30.131 g (0.5 mmol) of PPh. After the addition was completed, the mixture was purged with argon three times,Air was removed from the reaction flask, and then 15 ml of triethylamine, 1.96 ml of trimethylethynylsilane and 30 ml of tetrahydrofuran were added.After the addition was completed, the system was allowed to rise to 78 C for 20 h.The reaction mixture was filtered to remove a large amount of insoluble salts and solids. To the filtrate was added 150 ml of methylene chloride and the mixture was washed three times with 150 ml of 5% diluted hydrochloric acid. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. Ether to do the agent.After the column liquid was swirled to a white solid precipitation stopped rotating when placed at room temperature precipitated a large number of white solid, filtered and dried to give a white solid6-Methoxy-2-naphthylethynyltrimethylsilyl2.50 g, yield 98.4%

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; East China University of Science and Technology; Shen Dong; Liu Haipeng; Zheng Zhigang; (18 pag.)CN106336350; (2017); A;,
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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. 18800-30-1, name is 1-Bromo-4-(2-bromoethoxy)benzene, A new synthetic method of this compound is introduced below., category: ethers-buliding-blocks

b) 52.0 g (186 mmol) 1-Bromo-4-(2-bromoethoxy)benzene are added to 300 mL THF and cooled to 0 C. Within 30 min 25.0 g (223 mmol) KOtBu are added to this mixture in several portions. Cooling is removed and the reaction mixture is stirred at rt over night. The reaction is quenched by the addition of water. The resulting mixture is extracted with EtOAc (2×). The organic phases are combined, washed with brine, dried over MgSO4 and the solvent is removed in vacuo. The resulting product is used without further purification.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; ROTH, Gerald Juergen; FLECK, Martin; LEHMANN-LINTZ, Thorsten; NOSSE, Bernd; US2013/143876; (2013); 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. 588-96-5, name is p-Bromophenetole, A new synthetic method of this compound is introduced below., Quality Control of p-Bromophenetole

General procedure: CS127 was prepared using a modified literature procedure [16]. A solution of butyllithium (1. hexane, 0.15 mL) was added to a solution of 4-bromotoluene (8.52 mg, 0.050 mmol) in hexane (15 mL). After stirring for 1 h, N,N’-diisopropylcarbodiimide (6.29 mg, 0.050 mmol) was added dropwise. The solution was stirred for 1 h at room temperature and then the dimer [(FMeppy)2Ir(mu-Cl)]2 (30 mg, 0.025 mmol) was added. The mixture was heated overnight at 70 C. After being cooled to room temperature, the resulting precipitate was collected and washed with diethyl ether. The dried product was obtained as a yellow powder. Yield 65%.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Sahin, Cigdem; Goren, Aysen; Varlikli, Canan; Journal of Organometallic Chemistry; vol. 772; (2014); p. 68 – 78;,
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Adding a certain compound to certain chemical reactions, such as: 446-59-3, name is 2-Bromo-1-fluoro-3-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 446-59-3, COA of Formula: C7H6BrFO

A flame dried round bottle (evacuated under vacuum and filled with N2 ) was fitted with mechanical stirring, and charged with tert-butyl (S)-4-(6-chloro-8- fluoroquinazolin-4-yl)-3-methylpiperazine-1-carboxylate (685 mg, 1.80 mmol, 1.0 eq.) solution in dry THF. Bis(2,2,6,6-tetramethylpiperidinyl)zinc, lithium chloride, magnesium chloride complex ((TMP)2Zn?2 MgCl2?2 LiCl) (0.35 M solution in THF/toluene, 1.0 eq. ) was dropwise added. The reaction was allowed to stir for 45 min at RT and then degassed by bubbling nitrogen through the solution for 15 min. Solid 2- bromo-1-fluoro-3-methoxybenzene (1.0 eq.) and CPhos 3rd generation precatalyst (0.1 eq.) were added, and the resulting mixture was stirred at 40 C for 16 h. The reaction mixture was concentrated in vacuo, dissolved in ethyl acetate, cooled in an ice bath, and quenched with a 1:1 solution of saturated ammonium chloride and H2O. The layers were separated, and the aqueous layer was extracted with ethyl acetate. The combined organic layer was dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by flash column chromatography (stepwise gradient of 20%-30% EtOAc in hexanes) to afford the desired product (504 mg, 56% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-1-fluoro-3-methoxybenzene, and friends who are interested can also refer to it.

Reference:
Patent; ARAXES PHARMA LLC; LI, Liansheng; FENG, Jun; LONG, Yun Oliver; LIU, Yuan; WU, Tao; REN, Pingda; LIU, Yi; (335 pag.)WO2016/164675; (2016); A1;,
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Synthetic Route of 887581-09-1,Some common heterocyclic compound, 887581-09-1, name is (2-Bromo-5-methoxyphenyl)methanamine, molecular formula is C8H10BrNO, 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 25 mL Schlenk tube wascharged with a magnetic stirrer and DMSO (2.0 mL). Substituted(2-bromophenyl)methylamine (1) (0.5 mmol), amidine hydrochloride (2) (1.0 mmol),CuBr (0.1 mmol, 14.2 mg), and K2CO3 (1.5 mmol, 207 mg) were added to the tube.The mixture was stirred at 80-120 oC under nitrogen atmosphere for 24 h, and thenunder air for 0.5 h. The resulting mixture was cooled to room temperature and filtered,and the solid was washed with ethyl acetate for two times (3 × 3 mL). The combinedfiltrate was concentrated by the rotary evaporator, and the residue was purified bycolumn chromatography on silica gel using petroleum ether/ ethyl acetate as eluent togive the desired target product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (2-Bromo-5-methoxyphenyl)methanamine, its application will become more common.

Reference:
Article; Liu, Qing; Zhao, Yufen; Fu, Hua; Cheng, Changmei; Synlett; vol. 24; 16; (2013); p. 2089 – 2094;,
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Related Products of 944317-92-4, 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. 944317-92-4, name is 1-Bromo-4-fluoro-5-isopropyl-2-methoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A 500 mL dry flask was charged with 1-bromo-4-fluoro-5-isopropyl-2-methoxybenzene (BrMIP) (24.60 g, 0.10 mol) and dissolved in toluene (80 mL) and THF (80 mL). The resulting solution was flushed with argon, and tri- isopropylborate (32 mL, 0.1 mol) was added. The mixture was cooled to -80 C. Then 2.5 n-BuLi in hexanes (48 mL, 0.12 mol) was added slowly, maintaining a temperature below -55C. After completion of the n-BuLi addition, the reaction mixture was slowly warmed (1 hour) to -10C and water (120 mL) was added, followed by commercially available 2-bromo-5-(trifluoromethyl)benzonitrile (Formula VI’, X = Br, R2 = CN) (25.00 g, 0.10 mmol) and the catalyst, 1 , 1 bis( di-tertbutylphosphino)ferrocene palladium dichloride (265 mg, 0.8 mol%) addition. The organic layer turns dark brown immediately. The biphasic mixture is aged at room temperature with vigorous stirring for 12 hours. The aqueous layer was removed and the organic layer was washed with 1 M NaOH (aq) (100 mL), water (300 mL) and filtered through silica gel. The solvent was removed under reduced pressure to yield brown oil which was crystallized from EtOH/water (300/100 mL). The resulting slurry was filtered and the filter cake was washed with cold 50% EtOH. The product was dried at 40 C under vacuum to yield 4′-fluoro-5′- isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-carbonitrile (Formula VII’, Ri = CN, R2 = isopropyl) as a pale white solid (25.20 g, 75%). According to the same procedure in various scales and different concentrations of catalyst some other biaryl of Formula Vlh and Vll2 are prepared and listed in Table 3 and Table 4, respectively. For NMR data and melting points see Table 1 and 2.

The synthetic route of 1-Bromo-4-fluoro-5-isopropyl-2-methoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LEK PHARMACEUTICALS D.D.; HUMLJAN, Jan; MARAS, Nenad; WO2013/91696; (2013); A1;,
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18800-30-1, name is 1-Bromo-4-(2-bromoethoxy)benzene, 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. Computed Properties of C8H8Br2O

l-Bromo-4-(2-bromoethoxy)benzene (95 mg, 0.34 mmol) was added to a mixture of N-[2-(3-azetidinyloxy)-5,6-dichloro-3-pyridinyl]-2-chloro-4-pyridinecarboxamide (i.e. the product of Step C) (100 mg, 0.28 mmol) and N,N-diisopropylethylamine (76 mL, 0.42 mmol) in acetonitrile (3 mL), and the reaction mixture was heated at 60 C overnight. The cooled solution was treated with saturated aqueous sodium bicarbonate solution (2 mL) and water (2 mL), and then diluted with dichloromethane before being filtered through a tube containing Celite diatomaceous filter aid, eluting with dichloromethane. The residue after concentration was purified by chromatography (silica gel, ethyl acetate to 5% methanol in ethyl acetate) to give the title product, a compound of the present invention, as a pale yellow oil (84 mg)..H NMR delta 8.88 (s, 1H), 8.62 (d, 1H), 8.28 (br s, 1H), 7.77 (d, 1H), 7.62 (d, 1H), 7.37 (d, 2H), 6.78 (d, 2H), 5.35 (m, 1H), 3.99 (t, 2H), 3.92 (t, 2H), 3.42 (br s, 2H), 2.95 (t, 2H).

The synthetic route of 18800-30-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; CLARK, David Alan; LAHM, George, P.; WO2012/12366; (2012); A1;,
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