Tag: M.W=200-300

Application of 16799-05-6,Some common heterocyclic compound, 16799-05-6, name is 3-Chlorophenethyl Bromide, molecular formula is C8H8BrCl, 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.

a tert-Butyl {9-[2-(3-Chlorophenyl)ethyl]-4-methyl-1-methylthio-carbazol-2-yl}acetate Following a procedure and using relative proportions of starting materials similar to those described in Example 4, but using tert-butyl (4-methyl-1-methylthiocarbazol-2-yl)acetate and 2-(3-chlorophenyl)ethyl bromide as starting materials, the title compound was obtained in a yield of 73% as an oil.

The synthetic route of 16799-05-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sankyo Company, Limited; US5877199; (1999); A;,
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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. 61881-19-4, name is 2,2,2-Trifluoro-N-phenylacetimidoyl chloride belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C8H5ClF3N

General procedure: To an ice cooled suspension of NaH (3.3mmol) in dry THF (20mL) under nitrogen atmosphere was slowly added a solution of the ketone 8a-e(1mmol) in THF (5mL). The resulting suspension was stirred for 30min at 0C and then a solution of the corresponding trifluoroacetimidoyl chloride 9a-e (1mmol) in dry THF (3mL) was slowly added dropwise at 0C and then further stirred at room temperature for 3h. The resulting orange-brown solution was evaporated under reduced pressure, water was added carefully (20mL) and extracted with CHCl3 (2¡Á20mL). The organic extract was separated, dried over anhydrous magnesium sulfate and evaporated obtaining a brown oil, which was further purified either by recrystallization or column chromatography (silicagel, Hex 7: EtOAc 3).

The synthetic route of 61881-19-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Romero, Angel H.; Salazar, Jose; Lopez, Simon E.; Journal of Fluorine Chemistry; vol. 169; (2015); p. 32 – 37;,
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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. 38762-41-3, name is 4-Bromo-2-chloroaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 38762-41-3

To a solution of ?-MeO-9-BBN (1.0M in hexane, 22 mol) in THF (20 mL) at O0C was added n-propylmagnesium bromide (2.0M in ether, 10.5 mL). After 10 min, solvent was evaporated, and to the residue was added NMP (60 mL), Pd(dppf)Cl2 (1.0 mmol), 4-bromo-2-chloroaniline (20 mmol) and aqueous sodium carbonate (1.0M, 30 mL). The reaction was then heated at 95 0C overnight. The reaction mixture was diluted with ethyl acetate (150 mL), washed with water (20×3 mL) and saturated brine (20 mL). The organic layer was dried with MgSO4, filtered, and concentrated under reduced pressure. Flash chromatography of the residue (silica gel, slow gradient of 0-100% DCM in hexane) afforded 10.1. MS-ESI (pos.) m/z: 170 (M+H).

The synthetic route of 38762-41-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; WO2008/137027; (2008); A2;,
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Reference of 39226-96-5, 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 39226-96-5 as follows.

Example 76 /V-{[2-Chloro-3-(trifluoromethyl)phenyl]methyl}-3-methyl-2-oxo-1-(2- pyrazinyl)-4-imidazolidinecarboxamide (E76) (in a form obtainable or prepared from (4S)-2-oxo-3-{[(phenylmethyl)oxy]carbonyl}-4-imidazolidinecarboxylic acid); To a solution of 3-methyl-2-oxo-1-(2-pyrazinyl)-4-imidazolidinecarboxylic acid (145 mg, 0.561 mmol) and N-ethylmorpholine (0.426 ml, 3.36 mmol) in dichloromethane (5 ml) was added 1-hydroxybenzotriazole hydrate (86 mg, 0.561 mmol) and 1-ethyl-3- (3-dimethylaminopropyl)carbodiimide hydrochloride (107 mg, 0.561 mmol) and the reaction mixture was stirred for 10 minutes at room temperature. 1-[2-Chloro-3- (trifluoromethyl)phenyl]methanamine (141 mg, 0.673 mmol) was added and the reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with dichloromethane and washed with saturated sodium hydrogen carbonate solution, water and brine and separated by hydrophobic frit and the organic layer reduced under vacuum. The residue was purified by SP4 automated silica gel chromatography eluting with 10-100% ethyl acetate in isohexane to give N- {[2-chloro-3-(trifluoromethyl)phenyl]methyl}-3-methyl-2-oxo-1-(2-pyrazinyl)-4- imidazolidinecarboxamide (45 mg, 19 % yield). LC/MS [M+H]+ = 413, retention time = 2.21 minutes.

According to the analysis of related databases, 39226-96-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/119825; (2008); A2;,
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Application of 1435-50-3, These common heterocyclic compound, 1435-50-3, name is 2-Bromo-1,4-dichlorobenzene, 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.

General procedure: To a flask containing Mg turnings (0.29 g, 12 mmol) was added1-bromo-4-methylbenzene (1.37 g, 8.0 mmol) in THF (8 mL) at room temperature. After being stirred for 2 h, DMF (1.3 mL,12 mmol) was added to the reaction mixture. The obtained mixturewas stirred for 2 h at 0 C. Then, aq NH3 (7 mL, 28-30%) and I2 (4.06 g, 16 mmol) were added to the reaction mixture. After beingstirred for 2 h at room temperature, the reaction mixture waspoured into satd aq Na2SO3 solution and was extracted with CHCl3 (3*30 mL). The organic layer was dried over Na2SO4 and filtered.After removal of the solvent, the residue was purified by shortcolumn chromatography on silica gel (eluent: hexane/ethylacetate=9:1, v/v) to provide pure 4-methyl-1-benzonitrile (0.77 g) in 82% yield.

The synthetic route of 1435-50-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ishii, Genki; Harigae, Ryo; Moriyama, Katsuhiko; Togo, Hideo; Tetrahedron; vol. 69; 5; (2013); p. 1462 – 1469;,
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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. 329944-72-1, name is 3-Bromo-5-chlorotoluene, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 3-Bromo-5-chlorotoluene

S-Chloro-S-metbyl-benzonitrile To a stirred soiution of 1-Bromo-3-chloro-5-methyl- benzene (7 32g, 35 62mmol) in DMF (70ml), were added zinc cyanide (2.51g, 21 37mmol), DPPF (395mg, 0 712mmol), and Pd2dba3 (326mg, 0.356mmol) in this order. The flask was flushed with nitrogen and stirred in an oil bath (110-1200C) for 5hr After cooling to room temperature, the mixture was evaporated in vacuo. The residue was purified by silica gel column chromatography (eluent, etherhexane (from 1 ’19 to 1 9)) to afford 2.8g (51%) of a paie yellow solid m.p. 74-76 0C, 1H-NMR(200MHz, CDCi3) delta 2 39(3H s), 7 35(1 H, s), 7.40(1 HT s), 7.44(1 H, s), m/z (El) 151(M+).

According to the analysis of related databases, 329944-72-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; KIM, Choung, U.; MITCHELL, Michael, L.; SON, Jong, Chan; WO2010/9047; (2010); A1;,
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1127-85-1, name is 2,4-Dichloro-5,6,7,8-tetrahydroquinazoline, 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 2,4-Dichloro-5,6,7,8-tetrahydroquinazoline

2,4-dichloro-5,6,7,8-tetrahydroquinazoline (0.5 g, 2.46 mmol) was added to a round bottom flask and dissolved in tetrahydrofuran (30 mL), and furfurylamine (0.23 mL, 2.46 mmol) and triethylamine (1.03 mL, 7.39 mmol) were added thereto, followed by stirring at 60 C. for 1 hour. After completion of the reaction, the solvent was removed by distillation under reduced pressure and water was added to the reaction mixture. The resulting mixture was extracted with dichloromethane and dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography (ethyl acetate:hexane, 1:1, v/v) to obtain a compound (0.22 g, 34%); 1H NMR (400 MHz, CDCl3) delta 1.82 (s, 4H), 2.28 (s, 2H), 2.68 (s, 2H), 4.68 (d, J=4.8 Hz, 2H), 4.99 (s, 1H), 6.32 (d, J=12.4 Hz, 2H), 7.37 (s, 1H); 13C NMR (400 MHz, CDCl3) delta 21.82, 21.86, 21.91, 31.63, 38.20, 108.01, 110.53, 110.55, 142.37, 151.08, 157.37, 161.42, 164.43.

The synthetic route of 1127-85-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY; LEE, So Ha; YOO, Kyung Ho; ROH, Eun Joo; SIM, Tae Bo; KIM, Tae Young; KIM, Jae Ho; (30 pag.)US2019/315726; (2019); 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. 1099597-32-6, name is 2-Bromo-4-chlorobenzotrifluoride, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H3BrClF3

A mixture of Pd(PPh3)4 (2.20 g, 1 .94 mmol), Cul (0.74 g, 3.88 mmol), 2-bromo-4-chloro- 1 -(trifluoromethyl)benzene (Int 5a) (10.00 g, 38.76 mmol) and ethynyltrimethylsilane (13.30 g, 135.66 mmol) in TEA was stirred at 70 C overnight. The mixture was concentrated, EtOAc (200 mL) was added and the mixture was filtered through celite. The mixture was concentrated to dryness and the residue was purified by column chromatography (Hexane) to give the title compound as a yellow oil.

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; PHENEX PHARMACEUTICALS AG; DEUSCHLE, UIrich; STEENECK, Christoph; ALBERS, Michael; HOFFMANN, Thomas; (62 pag.)WO2018/153893; (2018); A1;,
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Electric Literature of 1940-29-0, A common heterocyclic compound, 1940-29-0, name is 4-Bromo-3,5-dichloroaniline, molecular formula is C6H4BrCl2N, 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.

A microwave vial containing 4-bromo-3,5-dichloroaniline (350 mg, 1.45 mmol, Eq: 1.00), 2- methoxypyridin-4-ylboronic acid (289 mg, 1.89 mmol, Eq: 1.3), sodium carbonate (394 mg, 3.72 mmol, Eq: 2.56) and bis(triphenylphosphine)palladium (II) chloride (65 mg, 92.6 flmol, Eq:0.0637) was degassed with Argon for 15 min. DME (8 mL) and water (2 mL) was added and the reaction was heated for 30 min with the microwave at 115 deg. The reaction mixture was concentrated, diluted with ethyl acetate, washed with brine, dried with sodium sulfate and chromatographed (40g Redisep, 100% to 10% ethyl acetate/hexane) to give 254 mg (65%) of desired product as a colorless oil.

The synthetic route of 1940-29-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BERTHEL, Steven Joseph; CHEN, Zhi; CHI, Feng; CHIN, Elbert; ERICKSON, Shawn David; GABRIEL, Stephen Deems; KOCER, Buelent; Mertz, Eric; PLANCHER, Jean-Marc; WEIKERT, Robert James; WO2014/135471; (2014); A1;,
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Synthetic Route of 57310-39-1, A common heterocyclic compound, 57310-39-1, name is 3-Bromo-4-chlorotoluene, molecular formula is C7H6BrCl, 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 2 4-Amino-l -(7H-pyrrolo[‘2,3-d1pyriniidin-4-ylVpiperidine-4-carboxylic acid (6- chloro-biphenyl-3-ylmethylVamide hydrochloride2A. 2-Chloro-5-methyl-biphenylA mixture of 2-bromo-l-chloro-4-methyl-benzene (4.83 g, 23.4 mmol), benzeneboronic acid (5.7 g, 46.7 mmol), Pd(Ph3P)4 (1.35 g, 1.2 mmol) and 2M Na2CO3 (34 mL) in DME (100 mL) was stirred at 1000C under N2 for 16 h. After cooling, the resulting suspension was filtered. The filtrate was diluted with saturated brine and extracted with ethyl acetate (2 x 150 mL). The combined organic layers were washed with brine (100 mL) and water (100 mL), dried (Na2SO4) and filtered through decolourising charcoal. After evaporation of the solvent, n-hexane was added to the oil. The mixture was filtered to remove solids and the filtrate was concentrated. The resulting crude oil was purified by silica column chromatography (ethyl acetate : n-hexane / 1 : 20) to give the title compound (1.76g, 90 %) as a light yellow oil. Rf= 0.55. GC-MS (EI) m/z 202.3 [M]+, Rt 3.41 min. 1H (500 MHz, CDCl3) delta 7.64 (IH, d, J = 7.5 Hz), 7.50-7.35 (5H, m), 7.15 (IH, s), 7.12 (IH, d, J = 7.5 Hz), 2.39 (3H, s).

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

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; THE INSTITUTE OF CANCER RESEARCH:ROYAL CANCER HOSPITAL; CANCER RESEARCH TECHNOLOGY LIMITED; ASTRAZENECA AB; WO2007/125325; (2007); A1;,
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