Tag: M.W=200-300

Some common heterocyclic compound, 344-65-0, name is 1-Bromo-4-chloro-2-(trifluoromethyl)benzene, molecular formula is C7H3BrClF3, 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. Computed Properties of C7H3BrClF3

General procedure: A 1,4-Dioxane solution (8 mL) of 10 (1.0 mmol), arylboronic acid 2 (1.0 equiv.), K3PO4, and Pd(PPh3)4 (5 molpercent) was heated at 75 C for 4 h. After cooling to room temperature, H2O was added and the reaction mixture was extracted with CH2Cl2. The organic layer was dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (pure n-heptane).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 344-65-0, its application will become more common.

Reference:
Article; Ali, Iftikhar; Siyo, Baraa; Hassan, Zahid; Malik, Imran; Ullah, Ihsan; Ali, Asad; Nawaz, Muhammad; Iqbal, Jamshed; Patonay, Tama?s; Villinger, Alexander; Langer, Peter; Journal of Fluorine Chemistry; vol. 145; (2013); p. 18 – 34;,
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Application of 62356-27-8,Some common heterocyclic compound, 62356-27-8, name is 1-Bromo-3-chloro-2-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.

EXAMPLE 4 6-(2-Bromo-6-chlorophenyl)-2-methylpyrido[2,3-d]-pyrimidin-7-amine A mixture of 20.0 g of 2-bromo-6-chlorotoluene [J. B. Cohen and M. S. Raper, J. Chem. Soc., 85: 1268 (1904)] and 18.0 g of N-bromosuccinimide in 200 ml of carbon tetrachloride is heated to reflux in the presence of 10 mg. of benzoyl peroxide as catalyst. After 24 hours, the mixture is cooled and filtered, and the filtrate is concentrated to dryness to give a lachrymatory oil which solidifies on standing, mp 56-60 C. Spectral data confirms that this crude product is primarily 6-chloro-alpha,2-dibromotoluene which is used in the subsequent reaction without further purification. A solution of 31.3 g of the crude 6-chloro-alpha,2-dibromotoluene in 100 ml of warm ethanol is treated with a solution of 6.7 g of potassium cyanide in 10 ml of water and the mixture is heated at reflux for 4 hours. The crude product is isolated by pouring the cooled reaction mixture into water and filtering the resulting precipitate. Recrystallization of this solid from aqueous ethanol then gives 12.4 g of 2-bromo-6-chlorophenylacetonitrile, mp 82-84 C. Following the procedure for Example 1, 2-bromo-6-chlorophenylacetonitrile is condensed with 4-amino-2-methylpyrimidin-5-carboxaldehyde to give 6-(2-bromo-6-chlorophenyl)-2-methylpyrido[2,3-d]-pyrimidin-7-amine, mp 272-274 C., after recrystallization from acetonitrile.

The synthetic route of 62356-27-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Warner-Lambert Company; US4271164; (1981); 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. 1127-85-1, name is 2,4-Dichloro-5,6,7,8-tetrahydroquinazoline, A new synthetic method of this compound is introduced below., Recommanded Product: 2,4-Dichloro-5,6,7,8-tetrahydroquinazoline

To THF (15 mL) were added (+/-)-trans-methyl 3-aminobicyclo[2.2.2]octane-2-carboxylate (0.68 g, 3.69 mmol), 2,4-dichloro-5,6,7,8-tetrahydroquinazoline (1.13 g, 2.46 mmol) and DIPEA (4.5 mL, 24.6 mmol). The mixture was stirred at 65 C overnight. The reaction mixture was quenched with water (100 mL). The resulting mixture was extracted with ethyl acetate (50 mL x 2). The combined organic layers were washed with saturated brine (80 mL), dried over ahydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (PE/EtOAc (v/v) = 4/1) to give the title compound as a white solid (862 mg, 17%).MS (ESI, pos. ion) m/z: 350.2 [M+H]+1H NMR (400 MHz, CDC13) (ppm): 4.75 (d, J = 5.1 Hz, 1H), 4.43 (t, J = 5.3 Hz, 1H), 3.77 (s, 3H), 2.68 (t, J= 5.9 Hz, 2H), 2.35 (d, J= 5.7 Hz, 1H), 2.29-2.23 (m, 2H), 2.05 (s, 1H), 1.96 (d, J = 2.5 Hz, 1H), 1.89-1.76 (m, 6H), 1.67-1.54 (m, 5H), 1.26 (d, J= 7.1 Hz, 1H).

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; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; REN, Qingyun; TANG, Changhua; LIN, Xiaohong; YIN, Junjun; YI, Kai; (270 pag.)WO2017/97234; (2017); 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. 627531-47-9, name is 4-Bromo-3-chloro-2-methylaniline, A new synthetic method of this compound is introduced below., SDS of cas: 627531-47-9

Into the compound 4-bromo-3-chloro-2-methylaniline 8.54g (39mmol) obtained in step 1 in 1L flask, it was stirred into 250ml of trifluoroacetic acid.Sikimyeo stirred at room temperature NaBH4out over the 9g (9 pellets) for 4 hours and stirred at room temperature for 16 hours.Refluxing the reaction solution at 100 and NaBH4were added to 4g (4 pellets).After completion of the reaction mixture was concentrated under reduced pressure, water (300ml) and ethyl acetate to remove the water layer after delamination to (300ml) and washed with 2N NaOH (300ml).The organic layer was washed with water and saturated NaCl solution and then MgSO4and concentrated under reduced pressure and dried by dehydration.Column to separate the concentrate to give the title compound 6g (40%).

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; DONG-A ST CO., LTD.; CHOI, SUNG PIL; CHOI, SEUL MIN; SON, BYOUNG HWA; KIM, HYUN JUNG; KIM, JU MI; JANG, BYUNG JUN; SUNG, JI HYUN; LEE, JI HYE; KIM, EUN JIN; KANG, KYUNG KOO; KIM, SOON HOE; (28 pag.)KR2015/123007; (2015); A;,
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Application of 60811-18-9,Some common heterocyclic compound, 60811-18-9, name is 4-Bromo-1-chloro-2-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.

3-{4-rhoiperidi?vloxv)phengammal]elhvi]oxv)~2-thlophe?ecarboxamideStep A – 1~Bromo-4-chioro-5-fluoro-2-rjitrobenzeneTo a solution of 4-bromo1-chioro-2-fluorobenzene (8.4 g, 40 mmoi) and ammonium nitrate in DCM (335 mL) at 00C was added TFA anhydride (41.3 mL) via addomegan funnel over 15 min. The reaction mixture was stirred at 0 0C for 15 min and then at rt for 2 h. The reaction was quenched with 560 ml saturated NaHCO3 solution and the layers separated. The aqueous layer was extracted with DCM and then EtOAc. The combined organic layer was dried over Na2SO4, filtered and silica gel was added, The volatites were evaporated under reduced pressure, and the residue was purified by flash column chromatography (0 to 15% EtOAc; hexane) to give 3.7 g (38%) of the title compound. 1H NMR (400 iVIHz, DMSO-cfe): delta 8.48 (d, J= 6.9 Hz1 IH), 8.18 (d, J= S-S Hz5 IH).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-1-chloro-2-fluorobenzene, its application will become more common.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2007/143456; (2007); A2;,
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These common heterocyclic compound, 210532-25-5, name is 3,5-Difluorobenzene-1-sulfonyl chloride, 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. Recommanded Product: 210532-25-5

To a suspension of 3-[2-(l,3-dioxo-l,3-dihydro-isoindol-2-ylmethyl)-benzoylamino]-6,6- dimethyl-5,6-dihydro-4H-pyrrolo[3,4-c]pyrazole-2-carboxylic acid ethyl ester hydrochloride (1.24 g, 2.4 mmol) in dry dichloromethane (30 mL) was added N,N- diisopropylethylamine (1.67 mL, 9.6 mmol) and 3,5-difluorobenzenesulfonyl chloride (0.77 g, 3.6 mmol). After stirring at room temperature for 3 hours the mixture was diluted with dichloromethane (50 mL), washed with IN HCl, water, saturated solution of NaHCC>3, brine, dried over sodium sulfate and evaporated to dryness. The crude was purified by flash chromatography on silica gel eluting with ethyl acetate and then with dichloromethane/methanol 98:2 affording the title compound as white solid (1.4 g).IH-NMR (400 MHz), delta (ppm, DMSOtZ6): 10.61 (bs, IH), 7.83 (m, 4H), 7.69-7.63 (m, 4H), 7.56-7.45 (m, 2H), 7.39 (m, IH), 5.05 (s, 2H), 4.72 (bs, 2H), 4.41 (q, J=7.1 Hz, 2H), 1.67 (s, 6H), 1.34 (t, J=7.1 Hz, 3H).

The synthetic route of 3,5-Difluorobenzene-1-sulfonyl chloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NERVIANO MEDICAL SCIENCES S.r.l.; WO2007/68637; (2007); A1;,
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Reference of 823-57-4,Some common heterocyclic compound, 823-57-4, name is 2-Bromo-5-chloroaniline, molecular formula is C6H5BrClN, 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 stirred solution of commercially available or known bromoaniline compound (1.0 mmol) inCH2Cl2 (5 mL) and the corresponding propiolic acid (1.3 mmol, 1.3 equiv) was addeddicyclohexyl carbodimide (DCC, 1.3 mmol, 1.3 equiv) at 0 ¡ãC. Then, the temperature wasgradually raised to 25 ¡ãC over 30 min. The mixture was stirred at the same temperature for 12 h,and diluted with EtOAc (50 mL) and sat. aq. NH4Cl (30 mL). The organic layer was separated,dried (Na2SO4), filtered and concentrated under reduced pressure. The crude residue was purified by column chromatography (silica gel, hexanes:EtOAc 8:1 or CH2Cl2 only) to affordpropiolamides 4-s, 5-s, 8a-s, 8b-s, and 10-s.

The synthetic route of 823-57-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Park, Sunhwa; Shin, Kye Jung; Seo, Jae Hong; Synlett; vol. 26; 16; (2015); p. 2296 – 2300;,
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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 14862-52-3 as follows. Recommanded Product: 3,5-Dibromochlorobenzene

To a stirred solution of 1,3-dibromo-5-chlorobenzene (600 mg, 2.20 mmol) and 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (455 mg, 2.20 mmol) in 1,4-dioaxane (15 mL) K2CO3 (920 mg, 6.60 mmol) was added and the mixture was degassed with argon for 20 minutes. Pd(PPh3)4 (76 mg, 0.06 mmol) was added to reaction mixture and degassed for another 20 minutes. The reaction mixture was refluxed under stirring for 8 hours and then filtered through celite pad. The filtrate was concentrated and the residue was purified by column chromatography on silica (100-200 mesh) eluting with 15% ethyl acetate in petroleum ether to afford the title compound as white solid (300 mg, 50 %).

According to the analysis of related databases, 14862-52-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Cortendo AB; Blass, B. E.; Abou-Gharbia, M. A.; Childers, W. E.; Iyer, P.; Boruwa, J.; (143 pag.)CN105722823; (2016); A;,
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Synthetic Route of 823-57-4,Some common heterocyclic compound, 823-57-4, name is 2-Bromo-5-chloroaniline, molecular formula is C6H5BrClN, 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.

Step B;. A solution of sodium nitrite (0.63 g, 9.2 mmol) and H2O (1.9 mL) was added dropwise at 0¡ã C. to a solution of 2-bromo-5-chlorobenzenamine (1.6 g, 7.7 mmol) in 12N HCl (18.2 mL) and TFA (2.31 mL). The reaction mixture was stirred at 0¡ã C. for 1 h followed by the dropwise addition of a solution of tin(II)chloride (3.1 g, 16.9 mmol) in 12N HCl (4.6 mL) and H2O (0.6 mL) at 0¡ã C. The reaction mixture stirred for 1 5 h at 20¡ã C. and was filtered and placed under vacuum to give 1 -(2-bromo-5-chlorophenyl)hydrazine hydrochloride (2.0 g, 7.8 mmol).

The synthetic route of 823-57-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Company; US2007/27178; (2007); A1;,
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97329-43-6, name is 1-Bromo-2-chloro-3-methylbenzene, 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: 97329-43-6

A mixture of l-bromo-2-chloro-3-methyl-benzene (3.0 g, 14.6 mmol), phenylmethanethiol (2.1 g, 17.5 mmol, 2.0 mL), (lE,4E)-l,5-diphenylpenta-l,4-dien-3- one;palladium (2.6 g, 2.9 mmol), DIEA (5.6 g, 43.8 mmol, 7.6 mL), and (5-diphenylphosphanyl- 9,9-dimethyl-xanthen-4-yl)-diphenyl-phosphane (1.6 g, 2.9 mmol) in dioxane (60.0 mL) was degassed and purged with 2 for 3 times, and then the mixture was stirred at 100C for 12 h under N2 atmosphere. The reaction mixture was concentrated under reduced pressure. The residue was purified by column chromatography (S1O2) to afford benzyl(2-chloro-3- methylphenyl)sulfane (2.6 g, 53.6% yield) as a yellow solid. 1HNMR (400MHz, CHLOROFORM-^ delta 7.44 – 7.37 (m, 2H), 7.36 – 7.23 (m, 3H), 7.16 – 7.03 (m, 3H), 4.42 – 3.93 (m, 2H), 2.73 – 2.22 (m, 3H).

The synthetic route of 97329-43-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; QUENTIS THERAPEUTICS, INC.; VACCA, Joseph P.; LI, Dansu; BETTIGOLE, Sarah; (214 pag.)WO2019/94641; (2019); A1;,
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