Month: July 2021

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. 3814-30-0, name is (Bromomethyl)cyclopentane, A new synthetic method of this compound is introduced below., Computed Properties of C6H11Br

Preparation 78 6-Bromo-1-(cyclopentylmethyl)-2-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridine Sodium hydride (60% in mineral oil, 10.8 mg, 0.271 mmol) was added to a solution of 6-bromo-2-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridine (Preparation 22, 50 mg, 0.180 mmol) in DMF (780 mL). The reaction mixture was then stirred for 15 minutes at room temperature before the addition of (bromomethyl)cyclopentane (44 mg, 0.271 mmol). The reaction mixture was then stirred overnight at room temperature and for 24 hours at 60 C. Sodium hydride (60% in mineral oil, 5 mg, 0.125 mmol) was added and the reaction was stirred for another 7 hours at 60 C. The reaction mixture was then diluted with water and EtOAc. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried (Na2SO4), filtered and concentrated under reduced pressure. The crude was purified via Biotage silica gel column chromatography eluting with (DCM/EtOAc 99/1 to 80/20) to afford the title product as a colourless oil (45 mg, 69%). 1H NMR (500 MHz, CDCl3) d 1.10-1.19 (m, 2H), 1.46-1.64 (m, 6H), 2.24-2.33 (m, 1H), 4.03 (s, 3H), 4.09 (d, J=7.6 Hz, 2H), 6.53 (d, J=0.9 Hz, 1H), 7.45 (t, J=0.9 Hz, 1H), 7.59 (s, 1H), 7.68 (s, 1H), 8.60 (d, J=0.9 Hz, 1H). LC (Method B)-MS (ESI, m/z) tR 3.03 min, 359 [(M+H+), 100%].

The synthetic route of 3814-30-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; Bavetsias, Vassilios; Atrash, Butrus; Naud, Sebastien Gaston Andre; Sheldrake, Peter William; Blagg, Julian; US2013/345181; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 7051-34-5,Some common heterocyclic compound, 7051-34-5, name is (Bromomethyl)cyclopropane, molecular formula is C4H7Br, 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-Hydroxybenzaldehyde (3.00 g, 0.0246 mol), bromomethylcyclopropane (3.58 ml, 0.0369 mol) and K2CO3 (6.8 g, 0.050 mol) were taken in acetone (80 ml) and refluxed for 24 h. The reaction mixture was cooled to room temperature, the insolubles filtered through Celite and the solvent was evaporated to obtain a crude residue. Purification of the residue by column chromatography (silica gel 60-120 mesh, EtOAc:Hexane 0.5:9.5) afforded 3.6 g (83.14%) of 4-cyclopropylmethoxybenzaldehyde. LCMS [M+H]+ 177.0 IH-NMR (CDCl3): 9.877 (s, IH), 7.813-7.833 (d, 2H, J=8 Hz), 6.984-7.004 (d, 2H, J=8 Hz), 3.882-3.899 (d, 2H, J= 6.8 Hz), 1.259-1.295 (m, IH), 0.669-.687 (m, 2H), 0.383 (bs, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (Bromomethyl)cyclopropane, its application will become more common.

Reference:
Patent; FOREST LABORATORIES HOLDINGS LIMITED; SARMA, Pakala, Kumara Savithru; ACHARYA, Vinod, Parameshwaran; KASIBHATLA, Srinivas, Rao; VISWANADHAN, Vellarkad, Narayana; SHEKHAR, Polisetti; BISCHOFF, Alexander; WO2010/127212; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 1435-51-4, These common heterocyclic compound, 1435-51-4, name is 1,3-Dibromo-5-fluorobenzene, 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.

l,3-Dibromo-5-fluorobenzene (10.2 g, 40.7 mmol) was dissolved in 1,4- dioxane. Pyridine-4-ylboronic acid (5 g, 40.7 mmol), tetrakis(triphenylphosphine)- palladium(O) (462 mg, 0.41 mmol), and K2CO3 (11.22 g, 81 mmol) were added, and the mixture was heated at 900C for 4 h. The reaction was diluted with EtOAc, washed with aq. NaHCO3 and dried and removed. Purification via column chromatography afforded 4-(3-bromo-5-fluorophenyl)pyridine (6 g, 59%). 1H NMR (400 MHz, CDCl3): delta 8.73 (d, IH), 8.58 (d, IH), 7.77 (dd, IH), 7.45 (s, IH), 7.34-7.31 (m, IH), 7.22 (t, IH), 7.18- 7.15 (m, IH).

Statistics shows that 1,3-Dibromo-5-fluorobenzene is playing an increasingly important role. we look forward to future research findings about 1435-51-4.

Reference:
Patent; SEPRACOR INC.; BURDI, Douglas; SPEAR, Kerry, L.; HARDY, Larry, Wendell; WO2010/114971; (2010); A1;,
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. 55289-36-6, name is 3-Bromo-2-methylaniline, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C7H8BrN

A mixture of sodium 2-(3-methoxypyridin-2-yl)acetate (0.166 g, 0.871 mmol), 3- bromo-2-methylaniline (0.1 18 mL, 0.958 mmol), DIEA (0.608 mL, 3.48 mmol) and HATU (0.397 g, 1.045 mmol) in DMF (4.0 mL) was stirred at room temperature. After 1 h, the mixture was diluted with EtOAc and washed twice with 10% aqueous LiCl, then with brine, dried and concentrated. The residue was purified by column chromatography on silica gel to provide N-(3-bromo-2-methylphenyl)-2-(3-methoxypyridin-2-yl) acetamide as a pale yellow solid (0.213 g, 73% yield). Mass spectrum m/z 335, 337 (M+H)+.

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 55289-36-6.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; KO, Soo Sung; BATT, Douglas A.; BERTRAND, Myra Beaudoin; DELUCCA, George V.; LANGEVINE, Charles M.; LIU, Qingjie; SRIVASTAVA, Anurag S.; WATTERSON, Scott Hunter; WO2014/210087; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 698-00-0, 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. 698-00-0, name is 2-Bromo-N,N-dimethylaniline, This compound has unique chemical properties. The synthetic route is as follows.

Synthesis of 2-(di-l-adamantylphosphino)-N^V-dimethylaniline (L2).[0287] Pd(OAc)2 (6.3 mg, 0.028 mmol) was added to a glass vial and dissolved in toluene (2 mL). This solution was then transferred to a vial containing DiPPF(l,l’-bis(diisopropylphosphino)ferrocene; 14.2 mg, 0.034 mmol) and was left to stir for 10 minutes. To a separate glass vial containing NaOtBu (192 mg, 2.0 mmol) was added a solution of (l-adamantyl)2PH (410 mg, 1.36 mmol) in 2 mL toluene, followed by2-bromo-NjV-dimethylaniline (230 L, 1.4 mmol), and the Pd(OAc)2/DiPPF solution, after which the vial was sealed with a cap containing a PTFE septum. The mixture was stirred for 20 h at 110 C, at which point the reaction was deemed complete on the basis of 31P NMR data obtained from an aliquot of the reaction mixture. The reaction mixture was then allowed to cool and was passed through a plug of silica, followed by washing of the plug with 40 mL of CH2C12. The combined eluent was collected and the solvent was removed in vacuo. The resulting pale orange solid was washed with cold hexanes (2 x 4 mL). Removal of volatile materials in vacuo yielded the product as an off-white powder (0.424 g, 1.01 mmol; 74 % yield). 1H NMR (CDC13): delta 7.71 (m, 1H, Ar-H), 7.32 (m, 1H, Ar-H), 7.20 (m, 1H, Ar-H), 7.05 (m, 1H, Ar-H), 2.71 (s, 6H, N(CH3)2), 2.01-1.89 (m, 18Eta, 1-Ad), 1.67 (s, 12Eta, 1-Ad). 13C{ ‘H} NMR (CDCI3): delta 161.6 (d, JPC = 21.6 Hz, Cquat), 137.4 (d, JPC = 3.3 Hz), 131.1 (d, JPC = 22.9 Hz, Cquat), 129.6, 122.2, 120.6 (d, Jpc = 3.9 Hz), 46.1 (d, Jpc = 4.2 Hz, N(CH3)2), 41.8 (d, Jpc = 13.0 Hz, CH2), 37.1 (CH2), 29.0 (d, /PC = 8.6 Hz, CH). 31P{ 1H} NMR (CDC13): delta 20.1. HRMS (ESI/[M+H]+) calcd. for C28H40N1P1: 422.2971. Found: 422.2978. Anal. Calcd for C^fttoPiNi: C 79.77; H 9.56; N 3.32. Found: C 79.47; H 9.46; N 3.31.

The chemical industry reduces the impact on the environment during synthesis 2-Bromo-N,N-dimethylaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; DALHOUSIE UNIVERSITY; LUNDGREN, Rylan, J.; STRADIOTTO, Mark; WO2012/68335; (2012); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 103273-01-4, A common heterocyclic compound, 103273-01-4, name is 2-Bromo-4-(tert-butyl)aniline, molecular formula is C10H14BrN, 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.

To a suspension of 4-trifluoromethylbenzoic acid (420 mg, 2.2 mmol) in dichloromethane (5 mL) was added N,N-dimethylformamide (1 drop) followed by oxalyl chloride (225 muL, 2.6 mmol) at 0 C. The mixture was warmed to room temperature and stirred for 4 hours before the volatile components were removed under a stream of nitrogen. The crude acid chloride was taken up in dichloromethane (2 mL) and added to a cooled solution of the aniline 39 (500 mg, 2.2 mmol) in dichloromethane (10 mL) and the mixture was stirred for 16 hours at room temperature. The reaction mixture was diluted with dichloromethane (20 mL), washed with saturated aqueous sodium hydrogen carbonate solution (2 x 20 mL) and saturated aqueous ammonium chloride solution (2 x 20 mL), dried over anhydrous magnesium sulfate and concentrated. The crude solid was purified by flash column chromatography using ethyl acetate, hexane (1:49 to 1:24) as an eluent and recrystallisation from isopropyl alcohol, water to obtain the title compound (660 mg, 75%) as a white solid, mp: 151.7-152.7 C; Rf: 0.63 (1:9 ethyl acetate, hexane); IR (vmax (film)): 3343, 2966, 1660, 1509, 1318, 1111, 1065 cm-1; 1H NMR (300 MHz, CDCl3): delta 1.31 (9H, s), 7.41 (1H, s), 7.79 (2H, d, J = 8.0 Hz), 8.04 (2H, d, J = 8.0 Hz), 8.31-8.45 (2H, m) ppm; 13C NMR (75 MHz, CDCl3): delta 31.4, 34.8, 114.1, 121.7, 123.6 (q, J = 270.0 Hz), 125.8, 126.2 (q, J = 3.6 Hz), 127.7, 129.4, 132.9, 133.2 (q, J = 31.2 Hz), 138.1, 149.6, 164.0 ppm; 19F NMR (282 MHz, CDCl3): delta -63.0 ppm; LRMS (+ESI) m/z: 422.0/424.0 ([M+Na]+ 100%); HRMS (ESI)+ Cald for C18H17BrF3NO [M+Na]+: 422.03378/424.03174, found 422.03396/424.03190.

The synthetic route of 103273-01-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Moir, Michael; Boyd, Rochelle; Gunosewoyo, Hendra; Montgomery, Andrew P.; Connor, Mark; Kassiou, Michael; Tetrahedron Letters; vol. 60; 36; (2019);,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 337915-79-4,Some common heterocyclic compound, 337915-79-4, name is 5-Bromo-N1-methylbenzene-1,2-diamine, molecular formula is C7H9BrN2, 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: HATU (4.89 g, 12.9 mmol) was added to a solution of the intermediate 4-bromo-N2-ethylbenzene-1,2-diamine, DIPEA (6.40 mL, 36.7 mmol), and cyclopropanecarboxylic acid (0.98 mL, 12.2 mmol) in DMF (40 mL), and the mixture was stirred at rt for 1 h. The mixture was quenched with water and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgSO4, and concentrated in vacuo. The residue was dissolved in AcOH (40 mL) and the mixture was stirred at 80 C for 1 h. After concentration of the mixture, the residue was neutralized with satd NaHCO3 solution and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by column chromatography (silica gel, hexane/EtOAc = 100/0 to 0/100) to give the title compound (1.2 g, 37%) as a pale yellow solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-N1-methylbenzene-1,2-diamine, its application will become more common.

Reference:
Article; Igawa, Hideyuki; Takahashi, Masashi; Shirasaki, Mikio; Kakegawa, Keiko; Kina, Asato; Ikoma, Minoru; Aida, Jumpei; Yasuma, Tsuneo; Okuda, Shoki; Kawata, Yayoi; Noguchi, Toshihiro; Yamamoto, Syunsuke; Fujioka, Yasushi; Kundu, Mrinalkanti; Khamrai, Uttam; Nakayama, Masaharu; Nagisa, Yasutaka; Kasai, Shizuo; Maekawa, Tsuyoshi; Bioorganic and Medicinal Chemistry; vol. 24; 11; (2016); p. 2486 – 2503;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 17247-58-4, name is (Bromomethyl)cyclobutane, 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 17247-58-4, Product Details of 17247-58-4

A solution of 12.3 g (83 mmol) of cyclobutylcarbinyl bromide (Aldrich) and 13.7 g (91 mmol) of sodium iodide in 150 mL of acetone was heated to reflux overnight and then cooled to room temperature. The inorganic solids were removed by filtration and the acetone and cyclopropylcarbinyl iodide (8.41 g, 46%) were removed by distillation (ambient temperature and 150 torr at 80 C., respectively). A solution of 4.0 g (21.98 mmol) of cyclobutyl carbinyl iodide in 30 mL of anhydrous diethyl ether cooled to -78 C. was cannulated into a solution of 17 mL (21.98 mmol) of 1.3M sec-butyllithium in cyclohexanes and the solution was stirred for 5 minutes. To this mixture was cannulated a solution of 3.0 g (21.98 mmol) of freshly distilled sulfuryl chloride in 110 mL of hexanes cooled to -78 C., the mixture warmed to room temperature over 1 hour and was then carefully concentrated in vacuo. This mixture was redissolved in diethyl ether, washed once with some ice-cold water, dried (MgSO4), filtered, and concentrated carefully. This mixture was redissolved in 30 mL of THF, added dropwise to 500 mL of saturated NH3 in THF and was allowed to stir overnight. The mixture was concentrated in vacuo to a crude yellow solid and was recrystallized from the minimum amount of dichloromethane in hexanes with 1-2 drops of methanol to afford 1.39 g (42%) of cyclobutyl carbinylsulfonamide as a white solid. 1H NMR (CDCl3) delta 1.81-2.03 (m, 4H), 2.14-2.28 (m, 2H), 2.81-2.92 (m, 1H), 3.22 (d, J=7 Hz, 2H), 4.74 (brs, 2H); 13C NMR (CDCl3) delta 19.10, 28.21, 30.64, 60.93; MS m/e 148 (M-1)-. time: 1.73, method B), 818 (M++H)

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; Bristol-Myers Squibb Company; US2008/14173; (2008); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 176317-02-5,Some common heterocyclic compound, 176317-02-5, name is 1-Bromo-2,3,4-trifluorobenzene, molecular formula is C6H2BrF3, 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 1 : tert-butyl 4-(2,3,4-trifluorophenyl)piperazine-l-carboxylate (1053) [00366] A mixture of A24-1C (200 mg, 0.95 mmol, 1 12.4 uL, 1.0 eq), A24-1D (21 1.9 mg, (1054) 1.1 mmol, 1.2 eq), Pd2(dba)3 (86.8 mg, 94.8 umol, 0.1 eq), BINAP (118. 1 mg, 0. 19 mmol, 0.2 eq) and f-BuONa (136.7 mg, 1.4 mmol, 1.5 eq) in toluene (5 mL) was degassed and purged with N2 for 3 times, and then the mixture was stirred at 100 C for 16 hour under N2 atmosphere. TLC showed Reactant A24-1C was consumed completely and one main new spot was detected. The reaction mixture was concentrated to give a residue. The residue was purified by column chromatography (Petroleum ether/Ethyl acetate= 1 :0-8: 1) to give compound A24-1B (250 mg, 790.3 umol, 83.4% yield) as a yellow oil. NMR (400 MHz, CDC13) delta 6.82 – 6.79 (m, 1H), 6.57 – 6.53 (m, 1H), 3.52 (t, J = 4.8 Hz, 4H), 2.91 (t, J = 4.8 Hz, 4H), 1.41 (s, 9H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-2,3,4-trifluorobenzene, its application will become more common.

Reference:
Patent; VIVACE THERAPEUTICS, INC.; LIN, Tracy Tzu-Ling Tang; KONRADI, Andrei W.; VACCA, Joseph; SHEN, Wang; COBURN, Craig; (231 pag.)WO2017/58716; (2017); 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. 65185-58-2, name is 2-Bromophenethylamine, A new synthetic method of this compound is introduced below., category: bromides-buliding-blocks

4m was then obtained by following the general procedure. A solution of compound 3 (160 mg, 0.81 mmol) in n-BuOH (6 mL) was treated with DIEA (114 mg, 0.89 mmol) and 2-chlorophenethylamine (162 mg, 0.81 mmol). Compound 4m was purified from this crude material by column chromatography (silicagel, n-hexane/EtOAc=3:1) (118.6 mg, 40.1%). 1H-NMR (400 MHz, DMSO-d6) delta 8.88 (t, J=5.2 Hz, 1H, N-H), 8.21 (d, J=7.6 Hz, 1H), 7.79 (t, J=8.4 Hz, 1H), 7.58 (t, J=15.6 Hz, 2H), 7.52 (t, J=8.4 Hz, 1H), 7.40-7.26 (m, 2H), 7.16 (td, J=8.6, 2.0 Hz, 1H), 3.70-3.60 (m, 2H, -CH2-), 3.11 (t, J=7.6 Hz, 2H, -CH2-). 13C-NMR (100 MHz, DMSO-d6) delta161.6, 157.4, 150.7, 138.8, 134.1, 133.0, 131.6, 129.0, 128.3, 127.1, 126.6, 124.5, 123.5, 114.0, 41.2, 34.8; LRMS (ESI) m/z: 363.2 ([M+H]+).

The synthetic route of 65185-58-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The Board of Regents of the University of Oklahoma; Wang, Weidong; Lee, Jae Wook; (35 pag.)US2019/47988; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary