Month: December 2020

These common heterocyclic compound, 1647-23-0, name is 1-Bromo-3,3-dimethylbutane, 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. 1647-23-0

The first step, weighed indole acetic acid (1.05g),Added to DMF (5 mL) and stirred to dissolve,Cooling to 0 ~ 5 C stirring;60% sodium hydride (0.72 g) was added,Stirring for 10min,3,3-dimethyl-1-bromobutane(1.5 g) was added,0 ~ 5 C reaction 0.5h,Slowly rose to room temperature reaction 2h;Add ethyl acetate (40mL), water (40mL); rapid mixing, 2min drop 6N hydrochloric acid solution 10mL,Stirring for 5 min; the phases were separated and the aqueous phase was extracted with ethyl acetate (20 mL). The phases were separated and the ethyl acetate phases were combined. Saturated brine(30 mL) for 5 min,The ethyl acetate phase was removed at 50 C under reduced pressure to give the crude product of the first step2- [1- (2-tert-butylethyl) -1H-indol-3-yl] acetic acid.

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 1647-23-0.

Reference:
Patent; Chinese Academy Of Medical Sciences Pharmaceutical Institute; Shi Jiangong; Guo Ying; Xu Chengbo; Chen Qing; Chen Minghua; Ba Mingyu; Zhu Chenggen; Tang Ke; Jiang Jiandong; Guo Jiamei; Guo Qinglan; Lin Sheng; Yang Yongchun; (44 pag.)CN107151223; (2017); A;,
Bromide – Wikipedia,
bromide – Wiktionary

40161-54-4, Adding some certain compound to certain chemical reactions, such as: 40161-54-4, name is 1-Bromo-2-fluoro-4-(trifluoromethyl)benzene, 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 40161-54-4.

Example 42: N-(5-Fluorothiazol-2-yl)-5-(2-(4-methylpiperazin-l-yl)-4- (trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(lH)-sulfonamide Step 1 : 5-(2-(4-Methyl-lH-imidazol-l-yl)-4-(trifluoromethyl)phenyl)isoquinoline A suspension of sodium hydride 60% (0.330 g, 13.75 mmol) in 8 mL DMF was cooled to 0 C and was treated with 4-methyl-lH-imidazole (0.676 g, 8.23 mmol). After stirring for 40 minutes, l-bromo-2-fluoro-4-(trifluoromethyl)benzene (1.180 ml, 8.23 mmol) was added, and the reaction mixture was heated to 120 C for 90 minutes. At this point Cl2Pd(AmPhos) (Sigma-Aldrich, St. Louis, MO, 0.291 g, 0.412 mmol), isoquinolin-5- ylboronic acid (1.424 g, 8.23 mmol), potassium phosphate (6.99 g, 32.9 mmol), 16 mL dioxane and 12 mL water were added, and the reaction mixture was heated to 120 C overnight. The reaction mixture was poured into saturated aHC03 solution and was extracted with DCM. The organics were concentrated then purified by reverse phase column chromatography [RediSep Gold C18 150g, 15 to 100% (0.1% NH40H in MeOH)/(0.1% NH40H in water)] yielding 5-(2-(4-methyl-lH-imidazol-l-yl)-4- (trifluoromethyl)phenyl)isoquinoline (1.435 g, 4.06 mmol) as an about 4: 1 mixture of isomers.

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 40161-54-4.

Reference:
Patent; AMGEN INC.; DINEEN, Thomas; KREIMAN, Charles; WEISS, Matthew; GEUNS-MEYER, Stephanie; WO2013/134518; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 2606-51-1, name is 5-(Bromomethyl)benzo[d][1,3]dioxole belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 2606-51-1

General procedure: The mixture of N-hydroxyhept-6-ynamide (141 mg, 1 mmol), benzyl bromide (256 mg, 1.5 mmol), sodium azide (98 mg, 1.5 mmol), copper(II) sulfate pentahydrate (38 mg, 0.13 mmol), sodium ascorbate (60 mg, 0.3 mmol) in wate and tert-butanol (v/v = 1:1, 10ml) was heated to 66 oC, the heterogeneous mixture was stirred vigrously for 24 h. After addition of water (50 ml), the mixture was filtered. The filter cake was dissloved in MeOH (20 ml), the insolubles was filtered, the filtrate was concentrated in vacuo and crystallized in ethyl acetate to give 2 (156 mg, 57%) as a white solid.

The synthetic route of 2606-51-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sun, Qiao; Yao, Yiwu; Liu, Chunping; Li, Hua; Yao, Hequan; Xue, Xiaowen; Liu, Jinsong; Tu, Zhengchao; Jiang, Sheng; Bioorganic and Medicinal Chemistry Letters; vol. 23; 11; (2013); p. 3295 – 3299;,
Bromide – Wikipedia,
bromide – Wiktionary

5003-71-4, 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. 5003-71-4, name is 3-Bromopropan-1-amine hydrobromide, This compound has unique chemical properties. The synthetic route is as follows.

TERT-BUTYL N-(3-BROMOPROPYL)CARBAMATE: was prepared from 3-bromopropylamine hydrobromide and BOC2O in the presence of base in dichloromethane.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Synaptic Pharmaceutical Corporation; US6727264; (2004); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

40161-54-4, 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. 40161-54-4, name is 1-Bromo-2-fluoro-4-(trifluoromethyl)benzene, A new synthetic method of this compound is introduced below.

General procedure: Benzimidazole (5 mmol), 1-bromo-2-fluorobenzene derivatives (15 mmol, 2 equiv) and tripottasium phosphate (5.31g, 25 mmol, 5 equiv) were dissolved in DMF (30 mL). The mixture was stirred at 150 C. The reaction time was determined by monitoring with TLC. The reaction mixture was diluted with CH2Cl2 (50 mL) and water (50 mL). The phases were separated, and the aqueous layer was extracted with CH2Cl2 (2 ¡Á 30 mL). The combined organic layerswere washed with water (3 ¡Á 50 mL), dried with MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (n-hexane/AcOEt).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Matsumura, Mio; Kitamura, Yuki; Yamauchi, Arisa; Kanazawa, Yoshitaka; Murata, Yuki; Hyodo, Tadashi; Yamaguchi, Kentaro; Yasuike, Shuji; Beilstein Journal of Organic Chemistry; vol. 15; (2019); p. 2029 – 2035;,
Bromide – Wikipedia,
bromide – Wiktionary

55289-36-6, name is 3-Bromo-2-methylaniline, belongs to bromides-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. 55289-36-6

To a solution of 10.0 g (53.7 mmol, 1.0 eq.) of 3-bromo-2-methylamine (LXXXVIIa) in 200 mL of acetonitrile at 0 C was added 42 mL of cone. HC1 followed by 42 mL of glacial acetic acid and a solution of 4.4 g (63.9 mmol, 1.1 eq.) of sodium nitrite in 12 mL of water. The mixture was purged with SO2 gas for 15 mm and a solution of 9.1 g (53.7 mmol, 1.0 eq.) ofcopper (II) chloride in 12 mL of water was added dropwise at 0 C. The mixture was allowed to warm to room temperature and stirred for 16 h. The mixture was concentrated in vacuo, diluted with 500 mL of water and extracted with 3 x 500 mL of ethyl acetate. The combined organic extracts were washed with 200 mL of sat. aqueous sodium bicarbonate solution, 200 mL of brine, dried (Na2SO4), filtered and the solvent was removed in vacuo. The residue waspurified by trituration with pentane to provide 8.0 g (29.7 mmol, 55%) of 3-bromo-2- methylbenzene-1-sulfonyl chloride (LXXXVIIIa). ?H NIVIR (400 MFIz, CDC13): 8.07 (d, 1H), 7.92 (d, 1H), 7.28 (t, 1H), 2.88 (s, 3H).

Statistics shows that 55289-36-6 is playing an increasingly important role. we look forward to future research findings about 3-Bromo-2-methylaniline.

Reference:
Patent; ARBUTUS BIOPHARMA CORPORATION; COLE, Andrew, G.; DORSEY, Bruce, D.; KAKARLA, Ramesh; KULTGEN, Steven; QUINTERO, Jorge; (353 pag.)WO2018/172852; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

38573-88-5,Some common heterocyclic compound, 38573-88-5, name is 1-Bromo-2,3-difluorobenzene, molecular formula is C6H3BrF2, 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.

4-(19): 1-(2,3-Difluorophenyl)-2-(1-(trityloxy)but-3-en-2-yloxy)ethanone Isopropylmagnesiumchloride-LiCl complex (1.30 M in THF, 155.0 mL, 0.0715 mol) under nitrogen was cooled to 0-5¡ã C., and 2,3-difluorobromobenzene (13.8 g, 0.0715 mol, 1.50 equiv.) was added while T<10¡ã C. After 1 h at 0-5¡ã C., a solution of 1-morpholino-2-(1-(trityloxy)but-3-en-2-yloxy)ethanone (21.8 g, 0.048 mol, 1.0 equiv.) in THF (2.0 vols) was added while T<10¡ã C. The reaction mixture was stirred for 2.5 h and monitored for consumption of 1-morpholino-2-(1-(trityloxy)but-3-en-2-yloxy)ethanone (target>97percent). The reaction mixture was quenched by charging into cold sat. aq. NH4Cl (110 mL) and water (33 mL) while T<20¡ã C. 2-Methoxy-2-methylpropane (218 mL) was added and the layers were separated. The organics were washed with sat. aq. NH4Cl (65 mL) and 18percent aq. NaCl (44 mL). The organics were concentrated under vacuum T<25¡ã C. to a light yellow oil (21.6 g). 1H NMR (500 MHz, CDCl3) delta ppm 7.70-7.64 (m, 1H), 7.47-7.42 (m, 6H), 7.37-7.30 (m, 1H), 7.30-7.25 (m, 6H), 7.24-7.19 (m, 3H), 7.19-7.13 (m, 1H), 5.84-5.71 (m, 1H), 5.30 (d, J=17.3 Hz, 1H), 5.25 (d, J=10.4 Hz, 1H), 4.78 (dd, J=17.7, 3.1 Hz, 1H), 4.70 (dd, J=17.7, 3.1 Hz, 1H), 4.03 (dd, J=11.8, 6.5 Hz, 1H), 3.35 (dd, 1=9.8, 6.4 Hz, 1H), 3.18 (dd, J=9.8, 4.6 Hz, 1H); 13C NMR (125 MHz, CDCl3) delta ppm 194.15 (dd, JCF=4.9, 2.4 Hz), 150.77 (dd, JCF=250.3, 14.1 Hz), 150.29 (dd, JCF=256.4, 13.9 Hz), 143.98, 135.34, 128.75, 127.76, 126.95, 125.70 (d, JCF=12.0 Hz), 125.16 (d, JCF=3.5 Hz), 124.55 (dd, JCF=6.4, 4.2 Hz), 121.62 (d, JCF=17.6 Hz), 118.83, 86.78, 81.35, 74.98 (d, JCF=9.5 Hz), 66.71. These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 38573-88-5, its application will become more common. Reference:
Patent; EISAI R&D MANAGEMENT CO., LTD.; Takaishi, Mamoru; Ishida, Tasuku; US2014/179690; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 4549-33-1, name is 1,9-Dibromononane, A new synthetic method of this compound is introduced below., 4549-33-1

General procedure: Finely ground KOH(4.48 g, 80 mmol) was added to a solution of pyrazole(2.72 g, 40 mmol) in DMSO (20 ml). The suspension wasthoroughly stirred for 30 min at 80, then treated bydropwise addition of 1,4-dibromobutane (4.32 g, 2.41 ml,20 mmol) in DMSO (10 ml) over 30 min, while cooling thereaction mixture with water. After finishing the addition ofdibrom derivative, stirring and heating at 80 wascontinued for additional 4 h, the reaction mixture wasthen poured into water (200 ml), extracted withchloroform (5¡Á10 ml), the extract was washed one timewith distilled water (10 ml) and dried over anhydrousCaCl2. Chloroform was removed by distillation undervacuum.

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; Zatonskaya, Lina V.; Schepetkin, Igor A.; Petrenko, Tatiana V.; Ogorodnikov, Vladimir D.; Khlebnikov, Andrei I.; Potapov, Andrei S.; Chemistry of Heterocyclic Compounds; vol. 52; 6; (2016); p. 388 – 401; Khim. Geterotsikl. Soedin.; vol. 52; 6; (2016); p. 388 – 401,14;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 38573-88-5, name is 1-Bromo-2,3-difluorobenzene, belongs to bromides-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 38573-88-5, 38573-88-5

Under a nitrogen atmosphere, 2,2,6,6-tetramethylpiperidine (48.5 mL) and THF (250 mL) were put in a reaction vessel, and the resulting mixture was cooled to 0¡ãC. Then, n-butyllithium (1.60 M; n-hexane solution; 178 mL) was slowly added thereto, and the resulting mixture was stirred for 1 hour. Next, the resulting mixture was cooled to -70¡ãC, and then a THF (500 mL) solution of compound (T-1) (50.0 g) was slowly added thereto, and stirred for 1 hour, and then N,N-dimethylformamide (DMF) (40.1 mL) was slowly added thereto, and stirred for 12 hours while the mixture was returned to room temperature. The resulting reaction mixture was poured into a saturated aqueous solution of ammonium chloride, and the resulting aqueous layer was subjected to extraction with ethyl acetate. Then, organic layers combined were washed with brine, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (hexane : ethyl acetate = 5 : 1 in a volume ratio). Then, the resulting product was further purified by recrystallization from a mixed solvent of hexane and ethyl acetate (1 : 1 in a volume ratio) to give compound (T-2) (46.9 g; 82percent).

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, 1-Bromo-2,3-difluorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JNC Corporation; JNC Petrochemical Corporation; TANAKA, Hiroyuki; ENDOU, Hiroshi; EP2957554; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

130723-13-6, 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 130723-13-6 as follows.

The 4-hydroxy-4-[3-(naphth-2-ylthio)-5-trifluoromethylphenyl]tetrahydropyran used as a starting material was obtained as follows: Sodium hydride (60% w/w dispersion in mineral oil; 0.5 g) was added portionwise to a mixture of 2-naphthalenethiol (1.42 g) and DMA (30 ml) and the mixture was stirred at ambient temperature for 1 hour. A solution of 1-bromo-3-fluoro-5-trifluoromethylbenzene (2.43 g) in DMA (10 ml) was added and the mixture was stirred at ambient temperature for 16 hours. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine (50 ml), dried (MgSO4) and evaporated. The residue was purified by column chromatography using hexane as eluent. There was thus obtained 3-bromo-5-trifluoromethylphenyl 2-naphthyl sulphide (1.37 g, 40%), as an oil. A solution of the product so obtained in THF (10 ml) was cooled to -60 C. and n-butyl-lithium (1.6M in hexane; 2.3 ml) was added dropwise.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 130723-13-6, and friends who are interested can also refer to it.

Reference:
Patent; Imperial Chemical Industries; ICI Pharma; US5208259; (1993); A;,
Bromide – Wikipedia,
bromide – Wiktionary