Tag: M.W=200-300

Electric Literature of 13526-66-4, 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 13526-66-4 as follows.

Example 1 (£)-2-(1-(3-((7-Fluoroquinolin-6-yl)methyl)imidazo[1 ,2-b]pyridazin-6-yl)ethylidene)- hydrazinecarboxamide6-Chloro-imidazo[1 ,2-b]pyridazin-3-yl)-(7-f luoro-quinolin-6-yl)-methanol (1.1 ) To a solution of 3-bromo-6-chloro-imidazo[1 ,2-b]pyridazine (13.27 g, 57.1 mmol) in 160 ml of THF was added EtMgBr (68.5 ml, 68.5 mmol) solution at room temperature. The reaction mixture was stirred for 30 min and a suspension of 7-Fluoro-quinoline-6-carbaldehyde (10 g, 57.1 mmol) in 40 ml of THF was added. The resulting mixture was stirred at roomtemperature for 3 hrs and quenched with 400 ml of water. After stirring for additional 1 hr, the precipitate was collected by filtration, washed with EtOAc and dried over vacuum oven overnight to afford 13 g (yield: 69%) of title compound. 1H-NMR (400MHz, DMSO-Cf6) delta ppm 8.91 (dd, 1 H), 8.49 (d, 1 H), 8.28 (d, 1 H), 8.24 (d, 1 H), 7.74 (d, 1 H), 7.54(q, 1 H), 7.51 (s, 1 H), 7.40 (d, 1 H), 6.54 (m, 2H).

According to the analysis of related databases, 13526-66-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; FU, Xingnian; HE, Feng; LI, Yue; LIU, Lei; MI, Yuan; XU, Yao-chang; XUN, Guoliang; YU, Zhengtian; ZHANG, Ji Yue (Jeff); DAI, Miao; WO2011/18454; (2011); 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. 13918-92-8, name is 2,4-Difluorobenzene-1-sulfonyl chloride, A new synthetic method of this compound is introduced below., Recommanded Product: 13918-92-8

General procedure: Compound 11a (800 mg,2.0 mmol) was dissolved in 10 ml ethyl acetate and then 9 N HCl(5 ml) was added, the reaction mixture was stirred for 30 min at roomtemperature, the reaction solvent was neutralized by NaHCO3 topH=8, 50 ml ethyl acetate and 30 ml H2O was added, after stirredadequately, the organic layer was separated, and concentrated, andthen the crude product was purified by silica gel columnchromatography using a mixture solvent of dichloromethane:methanol (20:1), to give white powder (540 mg); Above whitepowder (150 mg, 0.5 mmol) was dissolved in THF (10 ml),iodomethane (107 mg, 0.75 mmol) and triethylamine (0.5 ml) wereadded in the solvent. After the reaction mixture was stirred for 1 h at room temperature, the solvent was concentrated, the residues was purified by silica gel column chromatography using a mixture solvent ofdichloromethane: methanol (40:1), to give (12aa) Yield 49%, White powder.

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; Zhang, Min; Jiang, Li; Tao, Jia; Pan, Zhaoping; He, Mingyao; Su, Dongyuan; He, Gu; Jiang, Qinglin; Bioorganic and Medicinal Chemistry; vol. 27; 11; (2019); p. 2268 – 2279;,
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Application of 27139-97-5,Some common heterocyclic compound, 27139-97-5, name is 2-Bromo-4-chloro-1-methylbenzene, 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.

5-Chloro-2-methylbenzaldehyde Into a flame-dried 250 mL round-bottom flask equipped with a magnetic stir bar and under N2 was added 2-bromo-4-chlorotoluene (10.0 mL, 75.0 mmol) in anhydrous THF (150 mL). The clear sol. was cooled to -78° C. and BuLi (36.6 mL, 82.4 mmol, 2.25 M sol. in hexanes) was added dropwise over 20 min. The resulting light orange sol. was stirred at -78° C. for 1 h, and DMF (30 mL, 375 mmol) was added in a single addition. The resulting mixture was allowed to warm to rt over 4 h. The reaction was quenched by addition of aq. 1M HCl (20 mL), and stirred at rt overnight. The reaction mixture was poured into a 500 mL separatory funnel containing aq. 1M HCl (200 mL). The mixture was extracted with Et2O (3*100 mL). The combined org. layers were washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure to a yellow oil. Purification by short-path distillation under reduced pressure (1 mm Hg) yielded the title compound as a light yellow oil (7.99 g, 69percent). bp=70-72° C. at 1 mm Hg. 1H NMR (CDCl3, 500 MHz) delta 10.23 (1H, s), 7.77 (1H, d, J=2.5 Hz), 7.45 (1H, dd, J=8.0, 2.5 Hz), 7.22 (1H, d, J=8.0 Hz), 2.65 (3H, s).

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-4-chloro-1-methylbenzene, its application will become more common.

Reference:
Patent; Bezencon, Olivier; Bur, Daniel; Corminboeuf, Olivier; Dube, Daniel; Grisostomi, Corinna; MacDonald, Dwight; McKay, Dan; Powell, David; Remen, Lubos; Richard-Bildstein, Sylvia; Scheigetz, John; Therien, Michel; Weller, Thomas; US2009/176823; (2009); 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. 19752-55-7, name is 1-Bromo-3,5-dichlorobenzene, This compound has unique chemical properties. The synthetic route is as follows., Safety of 1-Bromo-3,5-dichlorobenzene

General procedure: A solution of aryl bromide (0.3 mol) (see Table 1) in diethyl ether (~215 mL) was added to a mixture of Mg turnings (7.29 g, 0.3 mol), diethyl ether (~17 mL), and a catalyst (several iodine crystals) under argon with stirring at such a rate that the ether was boiling, then the mixture was refluxed for 1?1.5 h. Since 1-bromo-2,4-dichlorobenzene (the starting compound for the synthesis of a-hydroxy ester 3e) did not react with magnesium under these conditions, the Grignard reaction for it was carried out in the presence of a large amount of iodine and dibromoethane (4 mL) upon reflux for 2.5 h.

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; Vasilyeva; Vorobyeva; Russian Chemical Bulletin; vol. 67; 8; (2018); p. 1426 – 1432; Izv. Akad. Nauk, Ser. Khim.; 8; (2018); p. 1426 – 1432,7;,
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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. 60811-21-4, name is 4-Bromo-2-chloro-1-fluorobenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C6H3BrClF

(2) The corresponding arylmagnesium bromide was prepared from 406 g (1.94 mol) of 4-bromo-2-chlorofluorobenzene and 48.6 g (2.00 mol) of magnesium turnings in 1,300 ml of anhydrous tetrahydrofuran by the customary process. The solution thus obtained was added dropwise to a solution of 278.3 g (2.3 mol) of allyl bromide in 200 ml of anhydrous tetrahydrofuran at 30-45 C. The mixture was then heated under reflux for 0.5 h, allowed to stand at room temperature for 16 h and poured onto 1.5 liters of ice-water. After acidification using a little 2N hydrochloric acid, the mixture was extracted twice using 1 liter of hexane each time. The extracts were washed three times with water, dried over Na2 SO4 and evaporated. The residue yielded 235 g (71%) of 3-(3-chloro-4-fluorophenyl)propene of b.p.10 =72 C. with a purity of 98.7% (determined by gas chromatography) on subsequent distillation.

The synthetic route of 60811-21-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hoechst Aktiengesellschaft; US4920212; (1990); A;,
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Electric Literature of 883499-24-9, 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. 883499-24-9, name is 1-Bromo-2-chloro-3-fluorobenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a mechanical-stirred solution of diisopropylamine (5.02 g, 7.08 ml, 49.7 mmol, Eq:1.04) in THF (35 ml) was added dropwise (5 mm) at -20C n-butyllithium, 1.6 M in hexane (31ml, 49.7 mmol, Eq: 1.04) and stirred at 0 C for 20 minutes. The mixture was cooled to -78 Cfollowed by dropwise addition (20 minutes) of a solution of 1-bromo-2-chloro-3-fluorobenzene(10 g, 47.7 mmol, Eq: 1) in THF (10 ml) and the thick yellow suspension was stirred at -78 Cfor 60 mm. Then was added dropwise (5 minutes – exotherm) N,N-dimethylformamide (5.23 g,5.55 ml, 71.6 mmol, Eq: 1.5), the cooling bath was removed and the mixture was allowed to warm to -20 C to give complete conversion. At -20 C the clear yellow solution was quenched with sat NH4C1 (100 ml) and extracted with TBME (100 ml). The aqueous layer was extracted again with TBME (50 ml). The organic layers were dried and evaporated at only 50 mbar forshort time. The yellow residue was dissolved in heptane/ethyl acetate 10:1 (ca. 30 ml) at 55 C,concentrated to 1/3 and stirred to 22 C while crystallisation started. After 30 minutes thesuspension was cooled to 0 C for 30 minutes, the solid was filtered off, washed with heptane (2x 15 ml) and dried (only short time) to give 4-bromo-3-chloro-2-fluorobenzaldehyde (5.27 g,47%) as light yellow solid. The filtrate was evaporated and purified by flash chromatography (silica gel, 70 g, adsorbed on isolute sorbent HM-N, EtOAc in heptane, 0% to 5% ) to give additional compound (4.073 g, 36%) as off-white solid.GC-MS: mlz = 235.9 M.+ (monoisotopic mass 235.90)

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

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; ALANINE, Alexander; BEIGNET, Julien; BLEICHER, Konrad; FASCHING, Bernhard; HILPERT, Hans; HU, Taishan; MACDONALD, Dwight; JACKSON, Stephen; KOLCZEWSKI, Sabine; KROLL, Carsten; SCHAEUBLIN, Adrian; SHEN, Hong; STOLL, Theodor; THOMAS, Helmut; WAHHAB, Amal; ZAMPALONI, Claudia; (623 pag.)WO2017/72062; (2017); A1;,
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Related Products of 39226-96-5, A common heterocyclic compound, 39226-96-5, name is (2-Chloro-3-(trifluoromethyl)phenyl)methanamine, molecular formula is C8H7ClF3N, 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.

Example 100 N-{[2-chloro-3-(trifluoromethyl)phenyl]methyl}-1-(2,2-dimethylpropyl)-5-oxoprolinamide (E100) 1-(2,2-dimethylpropyl)-5-oxoproline (0.100 g, 0.5 mmol, prepared as described below) was dissolved in dichloromethane (5 ml) and to this was added N-(3-dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (0.191 g, 1 mmol), and 1-hydroxybenzotriazole (0.135 g, 1 mmol). The mixture was stirred for 30 minutes at room temperature and then {[2-chloro-3-(trifluoromethyl)phenyl]methyl}amine (0.209 g, 1 mmol) was added and the mixture was stirred overnight at room temperature. The mixture was then washed sequentially with water, 3N aqueous citric acid, and three more times with water then dried by filtering through a hydromatrix cartridge (Varian 5 g). The solvent was then evaporated and the residue was purified by mass-directed automated HPLC to give pure N-{[2-chloro-3-(trifluoromethyl)phenyl]methyl}-1-(2,2-dimethylpropyl)-5-oxoprolinamide. LC/MS [M+H]+=391/393, retention time=2.78 minutes. N-{[2-chloro-3-(trifluoromethyl)phenyl]methyl}-1-(2,2-dimethylpropyl)-5-oxoprolinamide was prepared in an analogous manner to that described for example 100 but using 1-(2,2-dimethylpropyl)-5-oxoproline prepared as described below. LC/MS [M+H]+=391/393, retention time=2.76 minutes.

The synthetic route of 39226-96-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; US2008/9541; (2008); A1;,
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39226-96-5, name is (2-Chloro-3-(trifluoromethyl)phenyl)methanamine, 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. Recommanded Product: 39226-96-5

Example 51 N-{[2-chloro-3-(trifluoromethyl)phenyl]methyl}-1-methyl-5-oxoprolinamide 1-methyl-5-oxoproline (2.27 g, 15.88 mmol, prepared as described below) was dissolved in dichloromethane (150 ml) and to this was added N-(3-dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (3.35 g, 17.47 mmol), and 1-hydroxybenzotriazole (2.36 g, 17.47 mmol). The mixture was stirred for ~10 minutes and then triethylamine (2.21 ml, 15.88 mmol) and {[2-chloro-3-(trifluoromethyl)phenyl]methyl}amine (3.66 ml, 17.47 mmol) were added and the mixture was left stirring at room temperature overnight (~17 hrs). A white precipitate formed during this time. The mixture was then treated with saturated aqueous sodium hydrogen carbonate (~100 ml) and stirred for 10 minutes. The organic layer was separated using a hydrophobic frit and then 2N aqueous hydrogen chloride was added and mixed and separated again. The organic layer was concentrated to give white solids (~2.5 g). The solid was dissolved in ethyl acetate (~200 ml) and washed with water (4*50 ml) followed by brine (50 ml). The organic layer was then dried by passing through a phase separator and concentrated to give pure N-{[2-chloro-3-(trifluoromethyl)phenyl]methyl}-1-methyl-5-oxo-L-prolinamide as a fine white solid (2.48 g). LC/MS [M+H]+=335, retention time=2.24 minutes. 1H NMR (CDCl3, 500 MHz) delta 2.02 (m, 1H), 2.35 (m, 1H), 2.39 (m, 1H), 2.47 (m, 1H), 2.81 (s, 3H), 4.00 (dd, 1H, J=8.9, 4.2 Hz), 4.60 (dd, 1H, J=15.1, 6.2 Hz), 4.65 (dd, 1H, J=15.1, 6.2 Hz), 6.56 (broad t, 1H, J=5.8 Hz), 7.38 (t, 1H, J=7.7 Hz), 7.60 (dd, 1H, J=7.6, 1.0 Hz), 7.68 (dd, 1H, J=7.9, 1.2 Hz); 13C NMR delta 176.0, 171.5, 137.5, 133.9, 131.7, 129.3, 127.4, 127.0, 122.8, 63.8, 41.8, 29.4, 29.2, 23.4.

The synthetic route of 39226-96-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; US2008/9541; (2008); A1;,
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Reference of 33863-76-2,Some common heterocyclic compound, 33863-76-2, name is 1-Bromo-3-chloro-5-fluorobenzene, molecular formula is C6H3BrClF, 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.

steps 1 and 2-A solution of 1-bromo-3-chloro-5-fluoro-benzene (42a, 55 g, 263 mmol) was cooled to 0 C. and treated with a 25% methanolic sodium methoxide solution (68 mL, 315 mmol) and heated to 40 C. for 3 h. The solution was cooled and partitioned between water (1 L) and a 1:1 mixture of hexane/diethyl ether (3×200 mL). The combined extracts were washed with brine (60 mL), dried (Na2SO4), filtered and the solvents evaporated in vacuo to afford 42b as an oil (57.3 g, 92% pure, 238 mmol). The ether 42b (43 g, 173 mmol) was treated with glacial HOAc (150 mL) and 48% aqueous HBr (100 mL) and heated to 120 C. After 40 h, the volatiles were removed while heated to 80 C. and then cooled to RT. The residue was partitioned between water (100 mL) and DCM (3×250 mL). The combined extracts were washed with H2O (50 mL), aqueous NaHCO3 solution (2×50 mL), brine (50 mL), and (MgSO4). The solvents were removed to afford 23.3 g of 42c as a grey 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-Bromo-3-chloro-5-fluorobenzene, its application will become more common.

Reference:
Patent; Roche Palo Alto LLC; US2006/25462; (2006); A1;,
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Synthetic Route of 174913-12-3,Some common heterocyclic compound, 174913-12-3, name is 1-Bromo-3-chloro-5-methoxybenzene, molecular formula is C7H6BrClO, 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.

[00233] Step a: A solution of l-bromo-3-chloro-5-methoxybenzene (835 mg, 3.77 mmol), and l,3,5-trichloro-l,3,5-triazinane-2,4,6-trione (299 mg, 1.29 mmol) in DMF (18 mL) was stirred 16 h under N2 and 50 C. After cooling to RT, the reaction mixture was diluted with aqueous NH4C1 and extracted with Et20. The combined organic phases were dried over MgS04, filtered, concentrated, and the resulting residue was purified by silica chromatography (0 to 25% gradient of EtO Ac/heptane) to l-bromo-2,3-dichloro-5-methoxybenzene (720 mg, 2.81 mmol). NMR (400 MHz, CHLOROFORM-^ delta ppm 7.14 (d, J=2.76 Hz, 1 H), 7.01 (d, J=3.01 Hz, 1 H), 3.81 (s, 3 H).

The synthetic route of 174913-12-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; CHEN, Christine Hiu-tung; CHEN, Zhuoliang; FORTANET, Jorge Garcia; GRUNENFELDER, Denise; KARKI, Rajesh; KATO, Mitsunori; LAMARCHE, Matthew J.; PEREZ, Lawrence Blas; STAMS, Travis Matthew; WILLIAMS, Sarah; WO2015/107493; (2015); A1;,
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