Tag: M.W=200-300

Reference of 185122-74-1, 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. 185122-74-1, name is 5-Bromo-2,3-dihydro-1H-inden-1-amine belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

2.7 g of 5-bromoindan-1-ylamine were dissolved in 30 ml of dichloromethane. 2.2 g of pyridine were added to this solution followed by the addition of 1.4 g of propionic anhydride while cooling with ice. After returning the reaction solution to room temperature and stirring overnight, the reaction solution was poured into ice water and extracted with chloroform. The organic layer was washed with water and saturated brine followed by drying with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by silica gel column chromatography (developing solvent: ethyl acetate/n- hexane = 1/1 (volume ratio)) to obtain 2.4 g of the target compound. Yield: 70% 1H-NMR (CDCl3, deltappm): 1.20(t,3H), 1.73-1.85(m,1H), 2.25(q,2H), 2.55-2.65(m,1H), 2.80-3.00(m,2H), 5.41-5.59(m,2H), 7.14(d,1H) 7.33(d,1H), 7.3 8(s,1H)

The synthetic route of 5-Bromo-2,3-dihydro-1H-inden-1-amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nippon Soda Co., Ltd.; EP2186804; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 69321-60-4, 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. 69321-60-4, name is 2,6-Dibromotoluene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 35 2-(3-Bromo-2-methyl-phenyl)-6-dimethylamino-2H-isoquinolin-1-one 6-Dimethylamino-2H-isoquinolin-1-one (50 mg, 0.27 mmol), cuprous iodide (10 mg, 0.053 mmol), and potassium carbonate (37 mg, 0.27 mmol) were deposited in sealed vessel. 3 mL DMSO and 2,6-dibromotoluene (133 mg, 0.532 mmol) were added. Argon was bubbled through the mixture for 2 minutes and the lid was tightly closed. This was heated at 150 C. for 5 hours. The resulting mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, concentrated in vacuo, and purified by flash chromatography (30% ethyl acetate/hexanes) to yield 2-(3-Bromo-2-methyl-phenyl)-6-dimethylamino-2H-isoquinolin-1-one (43 mg, 0.12 mmol). MS (ESI) 357 (M+H)+.

The synthetic route of 2,6-Dibromotoluene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Roche Palo Alto LLC; US2010/4231; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

54962-75-3, name is 3-Bromo-5-(trifluoromethyl)aniline, 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. Application In Synthesis of 3-Bromo-5-(trifluoromethyl)aniline

In a reaction vessel, 24 g (0.1 mol) of 3-bromo-5-trifluoromethylaniline,8.2 g (0.1 mol) of 4-methylimidazole,58.7 g (0.18 mol) Cs2CO3,0.95 g (0.005 mol) CuI, 1.1 g (0.005 mol) D-glucosamine hydrochloride,Then 60 mL DMSO and 80 mL water were added,Stirring to dissolve, the reaction temperature was controlled at 90 ,The reaction was continued for 12 hours. After the reaction was completed, 120 mL of ethyl acetate was added,After centrifugation to take the supernatant,Concentration and drying gave 3- (4-methyl-1H-imidazol-1-yl) -5- (trifluoromethyl) aniline.The HPLC purity was 98.66% and the yield was 96.18%

The synthetic route of 54962-75-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhejiang Hui Neng Biological Co., Ltd.; Wen Ming; Xu Tianhua; Wu Zhonghua; He Qilei; (4 pag.)CN105949128; (2016); 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. 703-91-3, name is 5-Bromo-2-(trifluoromethyl)aniline, A new synthetic method of this compound is introduced below., Quality Control of 5-Bromo-2-(trifluoromethyl)aniline

N-(5-bromo-2-(trifluoromethyl)phenyl)acrylamide (2) : To a solution of 5-bromo- 2-(trifluoromethyl) aniline (1.4 g, 5.8 mmol) in dichloromethane (5.0 mL), diisopropylethylamine (1.2 mL, 6.5 mmol) and acryloyl chloride (0.6 g, 6.6 mmol) were added at -78 C. The resulting mixture was at 0 C for 2 h. After completion of reaction, the reaction mixture was concentrated under reduced pressure. The residue obtained was diluted with sodium bicarbonate solution and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford 2 (600 mg, 35%) as an off white solid. 1H NMR (400 MHz, DMSO-d6) : delta 5.783-5.788 (dd, J = 1.8, 10.2 Hz, 1H), 6.23-6.23 (dd, J = 1.8, 17.0 Hz, 1H), 6.52-6.54 (dd, J = 6.8, 17.0 Hz, 1H), 7.69 (m, 2H), 7.82 (s, 1H), 9.88 (brs, 1H). MS m/z (M+H): 294.0

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; CELGENE AVILOMICS RESEARCH, INC.; ALEXANDER, Matthew David; MCDONALD, Joseph John; NI, Yike; NIU, Deqiang; PETTER, Russell C.; QIAO, Lixin; SINGH, Juswinder; WANG, Tao; ZHU, Zhendong; WO2014/149164; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 4885-18-1, name is 1-(3-Bromophenyl)-N,N-dimethylmethanamine, 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 4885-18-1, Quality Control of 1-(3-Bromophenyl)-N,N-dimethylmethanamine

Example A135. (l R*.2S*)-2-(3-(3-((dimethylamino)methvnstyrvn-lH-indazol-6-yl)-5′- methoxyspiro[cyclopropane-l,3′-indolinl-2′-one 2,2,2-trifluoroacetate To a mixture of crude (l R*,2S*)-5′-methoxy-2-(3-vinyl-lH-indazol-6- yl)spiro[cyclopropane-l ,3′-indolin]-2′-one (100 mg, 0.2 mmol), l-(3-bromophenyl)-N,N- dimethylmethanamine (43 mg, 0.2 mmol), Pd(OAc)2 (2.2 mg, 0.01 mmol) and P(o-tol)3 (6.7 mg, 0.022 mmol) in DMF (2 mL) was added 1Pr2NEt (0.07 mL, 0.4 mmol). The resulting mixture was purged with argon, then microwaved 30 min at 125 0C. It was passed through a micro filter then purified by prep-HPLC to give the title compound as a light yellow solid. NMR indicated 7% branched isomer (43 mg, 37%). Spectral data was identical to that in obtained in Example A 134.

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; UNIVERSITY HEALTH NETWORK; SAMPSON, Peter Brent; Ll, Sze-Wan; LIU, Yong; PAULS, Heinz W.; EDWARDS, Louise G.; FORREST, Bryan T.; FEHER, Miklos; PATEL, Narendra Kumar B.; PAN, Guohua; WO2010/115279; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 13633-25-5, 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. 13633-25-5, name is 1-Bromo-4-phenylbutane belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 8d hydrochloride (0.15 g, 0.53 mmol), N-ethyldiisopropylamine(0.34 g, 2.7 mmol) and sodium hydride (0.07 g,1.8 mmol) in DMF (5 mL) was stirred for 0.5 h at rt. To the mixturewas added 4-phenylbutylbromide (0.50 g, 2.35 mmol) in an icebath,and the mixture was stirred for 2 h at 120 C. The mixturewas partitioned between ethyl acetate and water, and the aqueouslayer was extracted with ethyl acetate. The combined organic layerwas washed with brine, dried (Na2SO4) and concentrated in vacuo.The residue was purified by column chromatography on basic silicagel (n-hexane/EtOAc = 15/1-10/1) to produce pale brown oils, to asolution of which in ether (5 mL) was added 4 N HCl/EtOAc(0.15 mL, 0.6 mmol) dropwise in an ice-bath, and the precipitatewas filtered off to obtain 3g (0.15 g, 66%) as pale brown crystals.1H NMR (DMSO-d6) d 1.40-2.73 (14H, m), 2.80-3.40 (6H, m),3.87 (3H, s), 6.99-7.03 (2H, m), 7.16-7.32 (5H, m), 7.97 (1H, d,J = 8.4 Hz), 9.45 (1H, brs); Anal. Calcd for C25H32NO2ClHCl0.5H2O:C, 70.99; H, 7.86; N, 3.31. Found: C, 71.75; H, 8.26; N, 3.32; LC/MS(ESI) m/z 378 (M+H)+.

The synthetic route of 1-Bromo-4-phenylbutane has been constantly updated, and we look forward to future research findings.

Reference:
Article; Imaeda, Toshihiro; Ono, Koji; Nakai, Kazuo; Hori, Yasunobu; Matsukawa, Jun; Takagi, Terufumi; Fujioka, Yasushi; Tarui, Naoki; Kondo, Mitsuyo; Imanishi, Akio; Inatomi, Nobuhiro; Kajino, Masahiro; Itoh, Fumio; Nishida, Haruyuki; Bioorganic and Medicinal Chemistry; vol. 25; 14; (2017); p. 3719 – 3735;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 86845-27-4, name is 5-Bromo-2-methylbenzotrifluoride, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 86845-27-4

A mixture of 4-methyl-3-trifluorobromobenzene (33.26 g, 104.261 mmol) from step 1 above , KCN (20.43 g, 313.67 mmol) and tetrabutylammonium bromide (3.37 g, 10.45 mmol) in CH2CI2/H2O 1:1 (300 mL) was stirred at room temperature for 4 hours. The layers were separated and the organic layer washed with H2O (100 ml_) 1N HCI (100 ml_), brine, dried over Na2SO4 and then concentrated to a brown oil which was purified by flash column chromatography (0% to 20% EtOAc in hexanes) to give the product as a clear oil (14.9 g, 54%). 1H NMR (400 MHz, CDCI3) 6 3.91 (s, 2H), 7.57 (d, J=8.3 Hz, 1 H), 7.75 (dd, J=8.3, 2 Hz, 1 H), 7.84 (d, J=2 Hz, 1 H).

According to the analysis of related databases, 86845-27-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER INC.; WO2006/18725; (2006); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 1435-51-4,Some common heterocyclic compound, 1435-51-4, name is 1,3-Dibromo-5-fluorobenzene, molecular formula is C6H3Br2F, 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.

Preparation 4.; (4- (3-bromo-5-fluoro-phenyl)-cyclohex-3-enyl)-dimethyl-amine (enantiomer 2); Dissolve 1, 3-dibromo-5-fluoro-benzene (19.8 g, 77.90 mmol) in dry diethyl ether (300 mL) and cool to-60C. Add 1.6M n-BuLi in hexanes (50.9 mL, 81.44 mmol) dropwise over 15 min. and stir an additional 15 min. Add a pre-cooled (-60C) solution of 4-dimethylamino-cyclohexanone (10.0 g, 70.8 mmol) in diethyl ether (200 mL) dropwise over 30 min. Stir at-60C to-20C for 2 hr. , then warm to ambient temperature and stir for 1 hr. Quench the reaction with water (200 mL) and extract with ethyl acetate (3 x 200 mL). Dry over sodium sulfate, filter and concentrate. Purify the residue by flash chromatography (15% 2M NH3/MeOH in DCM) to obtain 1- (3-Bromo-5- fluoro-phenyl) -4-dimethylamino-cyclohexanol as a white foam (14. 5 g, 64.8%). MS (ES) m/z = 316 (M-H)-, 318 (M+H) +, 1H NMR (CDC13) : 8 7.41 (d, 1H, J= 2 Hz), 7.15 (m, 2H), 2.3 (m, 8H), 1.78 (m, 8H). Combine 1- (3-bromo-5-fluoro-phenyl)-4-dimethylamino-cyclohexanol (14.5 g, 45.9 mmol), p-TsOH (21.8 g, 114.6 mmol) and toluene (200 mL) and heat to reflux for 3 hr. Cool to ambient temperature and partition between ethyl acetate (500 mL) and 1M NaOH solution (250 mL). Wash the organic layer with 1M NaOH solution (200 mL) and saturated aqueous NaCl (200 mL), dry over sodium sulfate, filter and concentrate. Purify the residue by chromatography (silica gel, 10% 2M NH3/MeOH in DCM) to obtain (4- (3- bromo-5-fluoro-phenyl) -cyclohex-3-enyl) -dimethyl-amine (10.8 g, 79%): MS (ES) m/z= 298 (M-H)’, 300 (M+H) ; 1H NMR (CDC13) : 8 7.25 (d, 1H, J= 2 Hz), 7.02 (dd, 1H, J= 8 Hz, J= 2 Hz), 6.9 (dd, 1H, J= 8 Hz, J= 2 Hz), 6.04 (m, 1H), 2. 38 (m, 4H), 2.27 (s, 6H), 2.09 (m, 2H), 1.48 (m, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,3-Dibromo-5-fluorobenzene, its application will become more common.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/61439; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 7617-93-8, 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. 7617-93-8, name is 2-Bromo-1,4-bis(trifluoromethyl)benzene, This compound has unique chemical properties. The synthetic route is as follows.

Reference Example 30 1-[2,5-bis(trifluoromethyl)phenyl]pyrrolidin-3-ol; A solution of 2,5-bis(trifluoromethyl)phenyl bromide (4.45 g), 3-hydroxypyrrolidine (1.2 g), palladium(II) acetate (0.16 g), (+/-)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.87 g) and cesium carbonate (13.6 g) in toluene (74 mL) was stirred under an argon gas atmosphere at 80C for 16 hr. The reaction mixture was allowed to cool to room temperature, water was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate 90:10 – 75:25) to give the title compound (3.79 g, yield 91%) as an orange oil. 1H-NMR (300 MHz, CDCl3)delta:1.72 (d, J = 4.9 Hz, 1 H), 1.95 – 2.10 (m, 1 H), 2.10 – 2.24 (m, 1 H), 3.21 – 3.43 (m, 2 H), 3.60 – 3.78 (m, 2 H), 4.48 – 4.65 (m, 1 H), 7.01 – 7.16 (m, 1 H), 7.16 – 7.23 (m, 1 H), 7.63 – 7.74 (m, 1 H).

The chemical industry reduces the impact on the environment during synthesis 2-Bromo-1,4-bis(trifluoromethyl)benzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2295406; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 445-02-3,Some common heterocyclic compound, 445-02-3, name is 4-Bromo-2-(trifluoromethyl)aniline, molecular formula is C7H5BrF3N, 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.

Isopentyl nitrite (0. 67ML) was added dropwise to a solution of 4-bromo-2- (trifluoromethyl) aniline (1.2g) and dimethyl sulfide (0. 45ML) in acetonitrile (12ML). The reaction was slowly heated to reflux and then refluxed until gas evolution ceased. The volatiles were evaporated, the residue absorbed onto silica and the product eluted off with isohexane. YIELD 0. 8G. 1H NMR DMSO-d6: 8 7.59 (dd, 2H), 7.23 (d, 1H), 2.51 (s, 3H)

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-2-(trifluoromethyl)aniline, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; WO2004/89885; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary