Tag: M.W=200-300

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. 288251-96-7, name is 2-Isobutyl-5-nitrobenzonitrile, A new synthetic method of this compound is introduced below., Computed Properties of C11H12N2O2

To a mixture of 2-isobutyl-5-nitrobenzonitrile (500 mg, 2.9 mmol), cuprous bromide (86 mg, 0.6 mmol), cupric bromide (1.3 g, 5.8 mmol), hydrobromic acid (364 muL, 6.7 mmol) and acetonitrile (20 mL) in a 100 mL single-neck flask cooled in an ice bath was added a solution of sodium nitrite (242 mg, 3.0 mmol) in acetonitrile slowly. After stirred in the ice bath for half an hour, the mixture was slowly warmed to room temperature and stirred overnight. After the materials had all reacted when being determined by TLC, solvent was removed in vacuo, and saturated sodium chloride (20 mL) was added. The mixture was extracted with ethyl aceate (8 mL) and dried over anhydrous sodium sulfate. The organic layers were combined and concentrated in vacuo, and the cruded product was separated by a silica gel column (eluent: 100% of petroleum ether) to give a product (white solid, 260 mg), with a yield of 37.8%. 1H NMR (400 MHz, CDCl3) delta 7.72 (s, 1H), 7.61 (d, J = 8.4 Hz, 1H), 7.16 (d, J = 8.4 Hz, 1H), 2.66 (d, J = 7.3 Hz, 2H), 2.01 – 1.88 (m, 1H), 0.94 (d, J = 6.6 Hz, 6H).

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; Fudan University; WANG, Yonghui; HUANG, Yafei; QIU, Ruomeng; TANG, Ting; (68 pag.)EP3581561; (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. 105942-08-3, name is 4-Bromo-2-fluorobenzonitrile, A new synthetic method of this compound is introduced below., Computed Properties of C7H3BrFN

4-Bromo-2-phenoxy-benzonitrile (5c). Sodium hydride (12 g, 300 mmol) (60% by wt) was weighed into a flask and washed free of oil with several hexane rinsings. The hexanes were decanted and discarded and DMF was added to the flask. A solution of phenol (23.5 g, 250 mmol) in DMF (100 ml_) was added dropwise and the mixture was stirred at room temperature. To the mixture was added a solution of 4-bromo-2-fluoro-benzonitrile (50 g, 250 mmol, 100 ml_ DMF), dropwise. Upon complete addition, the reaction was refluxed for 20 h. The reaction was cooled to room temperature and poured into cold 1 N NaOH. A fine, tan precipitate formed and was collected by vacuum filtration to give Compound 5c. MS m/z (MH+) 277.

The synthetic route of 105942-08-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2007/30089; (2007); A1;,
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Reference of 1897-41-2,Some common heterocyclic compound, 1897-41-2, name is 2,3,5,6-Tetrachloroterephthalonitrile, molecular formula is C8Cl4N2, 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.

0.60 g (0.015 mol) of sodium hydroxide was added to a solution of 1.22 g (0.0075 mol) of 2,5-dichloropyridin-3-amine in 40 mL of DMF, followed by addition of 2 g (0.0075 mol) of 2,3,5,6-tetrachloroterephthalonitrile under stirring, the mixture was stirred for 5 h after addition at room temperature. After the reaction was over by Thin-Layer Chromatography monitoring, the reaction mixture was poured into water and extracted with ethyl acetate, the organic phase was washed with water and saturated brine, dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure. The residue was purified through silica column (ethyl acetate/petroleum ether (boiling point range 60-90° C.)=1:3, as an eluent) to give 2.21 g of compound C-118 as yellow solid, m.p. 202-204° C. [0194] 1H-NMR (300 MHz, internal standard TMS, solvent CDCl3) delta (ppm): 7.36 (d, J=2.4 Hz, 1H, Py-4-1H), 7.97 (d, J=2.4 Hz, 1H, Py-5-1H), 8.89 (br, 1H, NH).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,3,5,6-Tetrachloroterephthalonitrile, its application will become more common.

Reference:
Patent; SHENYANG RESEARCH INSTITUTE OF CHEMICAL INDUSTRY CO., LTD.; SINOCHEM CORPORATION; Liu, Changling; Huang, Guang; Lan, Jie; Hao, Shulin; Li, Zhinian; Li, Huichao; Guan, Aiying; Jiang, Airu; Xu, Ying; US2014/213598; (2014); A1;,
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Some common heterocyclic compound, 499983-13-0, name is 4-Bromo-3-fluorophenylacetonitrile, molecular formula is C8H5BrFN, 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: nitriles-buliding-blocks

A suspension of (4-bromo-3-fluorophenyl)acetonitrile (20 g; see step (ii) above) in cone. HCl (100 mL) was stirred at 8O0C overnight. The reaction mixture was basified with saturated NaHCO3 (aq.) and then extracted with ethyl acetate. The aqueous layer was acidified with cone. HCl and filtered to provide 8.2 g of the sub-title compound as a pink solid. This was employed directly in the next step without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 499983-13-0, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; WO2007/69986; (2007); 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. 925672-88-4, name is 5-Bromo-2-cyanobenzeneacetonitrile, This compound has unique chemical properties. The synthetic route is as follows., Safety of 5-Bromo-2-cyanobenzeneacetonitrile

1 ,6-Dibromoisoquinolin-3-amine. 4-Bromo-2-(cyanomethyl)benzonitrile(75 g, 339 mmol) was added to 2,2-dichloroacetic acid (150 mL, 339 mmol). The resulting solution was cooled to 0C in an ice-water bath. HBr (27.5 g, 339 mmol) was bubbled through the cold solution until a yellow precipitate crashed out of solution, resulting in a yellow slurry. HBr was bubbled through the slurry for an additional 5 minutes. The solution was allowed to warm to room temperature over 1 hour. The slurry was then cooled to 0C in an ice-water bath and diethyl ether (200 mL) was added. The mixture was stirred for 20 minutes at 5C. The product was recovered as a yellow solid by filtration (42 g, 41 %). LCMS (API-ES) m/z: 303 (M-^H+).

According to the analysis of related databases, 925672-88-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AMGEN INC.; WO2009/11871; (2009); A2;,
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Related Products of 140860-51-1,Some common heterocyclic compound, 140860-51-1, name is 2-Bromo-4-methoxybenzonitrile, molecular formula is C8H6BrNO, 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. To a stirred solution of tert-butyl 6-(methylsulfonamido)-4-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)isoindoline-2-carboxylate (1.030 g, 2.37 mmol) in l,4-dioxane:water (9: 1, 5 ml) were added K2C03 (0.300 g, 2.37 mmol) and 2-bromo-4-methoxybenzonitrile (CAS Number 140860- 51-1; 0.250 g, 1.185 mmol) at rt. The reaction mixture was degassed for 20 min before addition of PdCl2(dppf) (0.087 g, 0.118 mmol). The resulting reaction mixture was heated at 90C for 2 h. The reaction mixture was cooled to rt, poured into water (50 ml) and extracted with EtOAc (2 x 50 ml). The combined organic phase washed with brine (40 ml), dried over Na2S04, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography (8 % EtOAc in hexane) yielding tert-butyl 4-(2-cyano-5-methoxyphenyl)-6-(methylsulfonamido)isoindoline-2- carboxylate (0.150 g, 0.338 mmol). LCMS: Method A, 2.038 min, MS: ES+ 444.6; NMR (400 MHz, DMSO-d6) delta ppm 9.99 (s, 1H), 7.89 (t, J= 6.0 Hz, 1H), 7.23 – 7.10 (m, 4 H), 4.64 (d, J=11.2, 2 H), 4.42 (d, J=10.4, 2 H), 3.85 (s, 3 H), 3.02 (s, 3 H), 1.40 (d, J=15.6 Hz, 9 H).

The synthetic route of 140860-51-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MISSION THERAPEUTICS LIMITED; GIBSON, Karl Richard; JONES, Alison; KEMP, Mark Ian; MADIN, Andrew; STOCKLEY, Martin Lee; WHITLOCK, Gavin Alistair; WOODROW, Michael D; (241 pag.)WO2017/158388; (2017); A1;,
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Electric Literature of 90110-98-8,Some common heterocyclic compound, 90110-98-8, name is 3-Bromo-4-(hydroxymethyl)benzonitrile, molecular formula is C8H6BrNO, 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.

LiAlH4 (34.0 mmol; 34.0 mL of a 1.0 M solution in THF) was cooled to 0 C using an ice bath then treated with MeOH (102 mmol; 26.4 mL of a 3.86 M solution in THF) dropwise over 5 min. The product of Part 3C (0.900 g, 4.24 mmol) was then added and the resulting solution warmed slowly to ambient temperature as the ice bath melted. After 16 h total reaction time, the solution was diluted with H2O (9.0 mL) and the resulting suspension filtered through a scintered glass funnel of medium porosity. The solids were exhaustively washed with H2O and Et2O then transferred to a separatory funnel and split. The aqueous layer was further washed with Et2O and EtOAc and the combined organic layers dried over Na2SO4, filtered and concentrated in vacuo to a yellow solid (0.591 g), which was used without further purification in the subsequent reaction.

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-4-(hydroxymethyl)benzonitrile, its application will become more common.

Reference:
Patent; LANTHEUS MEDICAL IMAGING, INC.; RADEKE, Heike, S.; CESATI, Richard, R.; PUROHIT, Ajay; HARRIS, Thomas, D.; ROBINSON, Simon, P.; YU, Ming; CASEBIER, David, S.; HU, Carol, Hui; BROEKEMA, Matthias; ONTHANK, David, C.; WO2013/36869; (2013); A2;,
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Some common heterocyclic compound, 4592-94-3, name is 3-(4-Bromophenyl)-3-oxopropanenitrile, molecular formula is C9H6BrNO, 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 C9H6BrNO

General procedure: To a solution of catalyst 4 (0.01mmol), 3,5-(NO2)2C6H3CO2H (0.02mmol), and alpha,beta-unsaturated aldehyde 2 (0.10mmol) in toluene (1.0mL) was added alpha-cyanoketones 1 (0.15mmol) at 0C. The resulting solution was then stirred for 48h. After complete consumption of the aldehyde (as monitored by TLC), the reaction mixture was evaporated and then loaded onto silica gel (ethyl acetate/petroleumether=1:10 to 1:7) and the products 3a-n were obtained by column chromatography. 4.2.1 (4S)-6-(4-Bromophenyl)-2-hydroxy-4-phenyl-3,4-dihydro-2H-pyran-5-carbonitrile 3a The title compound was obtained according to the general procedure (87% yield) as a mixture of two diastereoisomers (major and minor). Yellow solid; [alpha]D30 = +22.6 (c 1.30, CHCl3); mp = 146-147 C; 1H NMR (400 MHz, CDCl3): delta 7.67 (d, J = 8.8 Hz, 2H; both diastereoisomers), 7.56 (d, J = 8.8 Hz, 2H; both diastereoisomers), 7.41-7.37 (m, 2H; both diastereoisomers), 7.32-7.29 (m, 3H; both diastereoisomers), 5.63 (s, 1H; major), 5.56 (s, 1H; minor), 3.94 (dd, J = 9.6, 6.4 Hz, 1H; major), 3.88 (dd, J = 10.0, 6.8 Hz, 1H; minor), 3.62 (s, 1H), 2.51-2.45 (m, 1H; minor), 2.29-2.23 (m, 1H; major), 2.09-2.03 (m, 1H; both diastereoisomers); 13C NMR (100 MHz, CDCl3): delta 162.1, 140.9, 132.0, 131.7, 129.8, 129.7, 129.2, 129.1, 127.9, 127.7, 127.5, 125.3, 119.0, 96.0, 92.6, 88.2, 40.3, 37.5, 36.6, 35.4 ppm; (additional peaks are observed due to diastereoisomers). IR (KBr): nu 3377.5, 2207.1, 1608.5, 1588.4, 1488.0, 1454.0, 1145.0, 1010.7, 954.9, 867.9, 829.8, 728.3, 700.9 cm-1; d.r.: trans/cis = 3.63/1; ESI-MS (m/z): 354.1 (M-H)-; HRMS(ESI): calcd for ([C18H14NO2BrNa+]): 378.0100. Found: 378.0086; enantiomeric excess: 96%, determined by HPLC (Chiralcel OD-H column, hexane/i-PrOH 80:20, flow rate 0.7 mL/min; lambda = 254 nm, tmajor = 17.5 min, tminor = 11.0 min).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4592-94-3, its application will become more common.

Reference:
Article; Niu, Zhiqiang; He, Xinwei; Shang, Yongjia; Tetrahedron Asymmetry; vol. 25; 10-11; (2014); p. 796 – 801;,
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Related Products of 179898-34-1,Some common heterocyclic compound, 179898-34-1, name is 3-Bromo-5-fluorobenzonitrile, molecular formula is C7H3BrFN, 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.

Intermediate T5: 3-fluoro-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile A mixture of 3-bromo-5-fluorobenzonitrile (0.300 g, 1.5 mmol), bis(pinacolato) diboron (0.762 g, 3 mmol), KOAc (0.589 g, 6.0 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.110 g, 0.15 mmol) in dioxane (15 mL) was stirred at 90 C. for 2 h. The solvent was removed and the residue was purified by flash chromatography on Biotage silica 50 g cartridge (cyclohexane to cyclohexane_EtOAc=70:30) to afford title compound (0.360 g, 1.46 mmol, 97% yield). 1H NMR (400 MHz, DMSO-d6) delta ppm 7.98-8.03 (m, 1H), 7.81-7.85 (m, 1H), 7.68-7.73 (M, 1H), 1.33 (s, 12H).

The synthetic route of 179898-34-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHIESI FARMACEUTICI S.P.A.; BIAGETTI, Matteo; ACCETTA, Alessandro; CAPELLI, Anna Maria; GUALA, Matilde; RETINI, Michele; US2015/361100; (2015); 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. 4592-94-3, name is 3-(4-Bromophenyl)-3-oxopropanenitrile, This compound has unique chemical properties. The synthetic route is as follows., Safety of 3-(4-Bromophenyl)-3-oxopropanenitrile

General procedure: A dry 50 mL round flask equipped with a magnetic stirring bar was charged with a solution of 3-oxo-3-phenylpropanenitrile (0.87 g, 6.0 mmol), benzaldehyde (0.61 mL, 6.0 mmol), piperidine (0.12 mL, 0.2 equiv), and acetic acid (0.069 mL, 0.2 equiv) in toluene (20 mL). The mixture was heated at 60 C for 12 h. After cooling to room temperature, the mixture was washed with water (10 mL) and the aqueous phase was extracted with ethyl acetate (3×10 mL). The crude mixture was subjected to column chromatography (PE/EA 98:2) to yield 0.68 g (2.9 mmol, 48%) of the desired product as a white solid.

According to the analysis of related databases, 4592-94-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Liu, Wen; Zhou, Jing; Zheng, Changwu; Chen, Xingkuan; Xiao, Hua; Yang, Yingquan; Guo, Yinlong; Zhao, Gang; Tetrahedron; vol. 67; 10; (2011); p. 1768 – 1773;,
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