Tag: M.W=100-200

Application of 4117-09-3, 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. 4117-09-3, name is 7-Bromo-1-heptene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 1 Synthesis of Nonenoic Acid (Compound 19) Sodium ethoxide was added to a solution of diethylmalonate in ethanol. To this solution was added 1-bromo-hept-6-ene. The reaction mixture was concentrated and then treated with aqueous potassium hydroxide. The reaction mixture was acidified and then heated at 140 C. to ensure decarboxylation and give nonenoic acid (19).

The synthetic route of 7-Bromo-1-heptene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Achillion Pharmaceuticals Inc.; Phadke, Avinash; Hashimoto, Akihiro; US9006423; (2015); B2;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 766-81-4, 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. 766-81-4, name is 3-Bromophenylacetylene, This compound has unique chemical properties. The synthetic route is as follows.

In 25 ml in the reactor, adding O-bromophenyl (0.034 g, 0.2 mmol) and cuprous iodide (0.004 g, 0 . 02 mmol) butyl potassium (0.045 g, 0.4 mmol), vacuum replace the nitrogen after three times by adding 3 – bromophenylacetic acetylene (0.054 g, 0.3 mmol) and water (0.015 g, 0.8 mmol), in anhydrous 1, 4 – dioxane 1.5 ml, 110 C under stirring 16 h after. Column chromatography (silica gel, 200 – 300 mesh; developing agent, petroleum ether: ethyl acetate=5:1) to obtain 3 – (3 – bromophenylacetic methylene) isoindoline -1 – one 0.042 g, yield 70%.

The chemical industry reduces the impact on the environment during synthesis 3-Bromophenylacetylene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Dalian University of Technology; Bao Ming; Li Pengcheng; Zhang Sheng; Wang Wanhui; (24 pag.)CN109912492; (2019); A;,
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. 10269-01-9, name is (3-Bromophenyl)methanamine, A new synthetic method of this compound is introduced below., Product Details of 10269-01-9

Example 1. Synthesis of iV2-{[3′-(aminomethyl)biphenyl-3-yl]methyl}-iV4-{[mM5-4- (aminomethyl)cyclohexyl]methyl}-5-nitropyrimidine-2,4-diamine; To a mixture of 2,6-dichloro-5-nitropyrimidine (17.13 g, 88.30 mmol) and CH3CN (50 mL) at 0 0C was added a mixture of ^ra«5-(4-aminomcthyl-cyclohcxylmcthyl)-carbamic acid tert-butyl ester (21.40 g, 88.30 mmol) and lambdazetaN-diisopropylethylamine (15.4 mL, 88.30 mmol) in CH3CN (50 mL). The reaction mixture was allowed to warm to room temperature and stirred overnight. Volatiles were evaporated in vacuo and the residue purified by silica gel chromatography (Hexane/EtOAc 4:1) to afford tr°«5-4-[(2-chloro-5- nitro-pyrimidin-4-ylamino)-methyl]-cyclohexylmethyl}-carbamic acid tert-buty] ester (25.00 g, 71%) as an off-white solid.To a solution of 3-bromo-benzylamine (716 mg, 3.85 mmol) and. diisopropylethylamine (0.65 mL, 3.75 mmol) in dichloromethane (25 mL) was added /ralpha«lambda’-4-[(2-chloro-5-nitro- pyrimidin-4-ylamino)-methyl]-cyclohexylmethyl}-carbamic acid tert-butyl ester (1.01 g, 2.53 mmol). The rxn mixture was stirred at room temperature for 17 h, then partitioned between ethyl acetate and IM HCl solution. The organic phase was washed with satd NaHCtheta3 solution and brine, dried over Na2SO4, filtered and concentrated. The crude product was purified by silica gel chromatography eluting with 0-3% MeOH in CH2Cl2 to afford 723 mg (52%) of (trans-4-{[2-(3-bromo-benzylamino)-5-nitro-pyrimidin-4- ylamino] -methyl) -cyclohexylmethyl)-carbamic acid tert-butyl ester as a pale yellow solid, m/z 549.3 (M + H)+.To a mixture of (fralphan>s-4-{[2-(3-bromo-benzylam.mo)-5-nitro-pyrimidin-4-ylamino]- methyl}-cyclohexylmethyl)-carbamic acid tert-butyl ester (50 mg, 0.091 mmol), (3- aminomethylphenyl)boronic acid HCl (26 mg, 0.137 mmol), tetrakis(triphenylphosphine)palladium (10 mg, 0.009 mmol), and sodium carbonate (38 mg, 0.360 mmol) was added dimethoxyethane (1.0 mL) and water (0.150 mL). The reaction mixture was sealed under N2 and heated at 90 0C for 5 h. The reaction mixture was partitioned between ethyl acetate (20 mL) and water (5 mL). The organic phase was washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel chromatography eluting with 0-80% 0.1 :1 :9 NH4OH/MeOH/CH2Cl2 in CH2Cl2 to furnish 21 mg (40%) of [?ralphar°-4-({2-[(3′-aminomethyl-biphenyl-3-ylmethyl)- amino]-5-nitro-pyrimidin-4-ylamino} -methyl)-cyclohexylmethyl]-carbamic acid tert-butyl ester as a yellow oil, m/z 576.4 (M + H) ‘ . ” A solution of [tralpha«lambda’-4-({2-[(3′-aminomethyl-biphenyl-3-yhnethyl)-amino]-5-nitro- pyrimidin-4-ylamino}-methyl)-cyclohexylmethyl]-carbamic acid tert-butyl ester (21 mg, 0.036 mmol) in dichloromethane (4.0 mL) was treated with 4 M HCl in dioxane (0.100 mL, 0.400 mmol). The reaction mixture was stirred at room temperature for 18 h and then concentrated. The crude product was purified silica gel chromatography eluting with 0- 100% 0.1:1:9 NH4OH/MeOH/CH2Cl2 in CH2Cl2 to give 16 mg (93%) of N2-{[3′-(aminomethyl)biphenyl-3-yl]methyl} -N4- {[trans-4-(aminomethyl)cyclohexyl]methyl} -5- nitropyrimidine-2,4-diamine, m/z 476.5 (M + H)+.

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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2007/76247; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 2924-09-6, These common heterocyclic compound, 2924-09-6, name is 5-Bromo-2-fluoroaniline, 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 vial was charged with 5-bromo-2-fluoroaniline (1 g, 5.26 mmol), bis(pinacolato)diboron (1.6 g , 6.31 mmol), potassium acetate (1.03 g, 10.52 mmol), Pd(dppf)Cl2 · CH2C12 (129 mg, 0.158 mmol), and DMF (10 mL) under nitrogenatmosphere. After stirring for 2 h at 100 C the reaction mixture was concentrated in vacuo, the residue was triturated with EtOAc and filtered through a pad of celite. The filtrate was adsorbed on silica gel. Purification by flash silica gel chromatography using a gradient of 0- 30% EtOAc/hexane afforded 1.25 g of pinacol 3-amino-4-fluoroboronate as a light yellow oil (quant.): 1H NMR (CDC13, ppm) delta 1.36 (s, 12H), 3.71 (broad s, 2H), 7.00 (dd, 1H), 7.19 (m, 1H), 7.26 (dd, 1H); [M+H]+ m/z 238.

Statistics shows that 5-Bromo-2-fluoroaniline is playing an increasingly important role. we look forward to future research findings about 2924-09-6.

Reference:
Patent; SELEXAGEN THERAPEUTICS, INC.; VERNIER, Jean-michel; HOPKINS, Stephanie; BOUNAUD, Pierre-Yves; O’CONNOR, Patrick; MATTHEWS, David; BENDER, Steve; WO2012/125981; (2012); A2;,
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. 766-81-4, name is 3-Bromophenylacetylene, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H5Br

Step b); Preparation of 1-(3-bromo-phenyl)-2-[5-propionyl-1-(2,2,2-trifluoro-ethyl)-1H-pyrrole-3-yl]-ethane-1,2-dione; A mixture of 1-[4-Iodo-1-(2,2,2-trifluoro-ethyl)-1H-pyrrole-2-yl)-propan-1-one (4.8 g, 0.145 mol), 1-bromo-3-ethynyl-benzene (2.62 g, 0.145 mol) CuI (137 mg, 0.725 mmol) and Pd(PPh3)4 (670 mg, 0.58 mmol) in a mixture of triethylamine (50 ml) and acetonitrile (20 ml) is heated to reflux for 2 hours before cooled down to room temperature. The volatile solvent is removed under reduced pressure, and the residue is partitioned between ethyl acetate (50 ml) and water (200 ml). The organic phase is dried with MgSO4 and is purified by flash chromatography with EtOAc/hexane (10/90-20/80) as eluent to afford the alkyne product as a yellow solid 4.6 g (82%). This solid stirred with KMnO4 (4.73 g, 2.5 mol), NaHCO3 (604 mg, 7.2 mmol) and MgSO4(2.16 g, 18 mmol) in a mixture of acetone (200 ml) and water (100 ml) at room temperature for two hours. The mixture is extracted with ether (2×50 ml) to afford the product as a yellow oil 4.5 g (90%). 1HNMR (DMSO-d6): delta (ppm) 1.03 (t, 3H), 2.92 (q, 2H), 5.38 (q, 2H) 7.56 (t, 1H), 7.74 (s, 1H), 7.92 (d, 1H), 7.95 (d, 2H), 8.06 (s, 1H), 8.12 (s, 1H).

The synthetic route of 766-81-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wyeth; US2007/4786; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 399-94-0, A common heterocyclic compound, 399-94-0, name is 1-Bromo-2,5-difluorobenzene, molecular formula is C6H3BrF2, 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.

Reference Example-71 THF (25 mL) was added to metal magnesium (2.55 g, 105 mmol), and 2-bromo-1,4-difluoro benzene (19.70 g, 100 mmol) was slowly added thereto, whereby a Grignard reagent was prepared. The previously prepared Grignard reagent was added dropwise to the separately prepared solution of diethyl oxalate (15.34 g, 105 mmol) in THF (10 mL) at -40 C. or lower. After the dropping was completed, the reaction temperature was raised to 0 C., followed stirring for 1 hour. A saturated ammonium chloride aqueous solution and water (200 mL) were added to the reaction solution, and the resultant product was extracted with ethyl acetate (200 mL*2). After the organic layer was dried over magnesium sulfate and filtered, the solvent was distilled off under reduced pressure, and the resultant product was distilled under reduced pressure, whereby ethyl 2-(2,5-difluorophenyl)-2-oxoacetate (14.82 g, yield: 62%) was obtained as a colorless liquid. 1H-NMR (400 MHz, CDCl3): delta1.40 (t, J=7.0 Hz, 3H), 4.44 (q, J=7.0 Hz, 2H), 7.16 (ddd, J=9.3, 9.3 and 4.0 Hz, 1H), 7.34 (dddd, J=9.3, 9.2, 7.3 and 3.3 Hz, 1H), 7.60 (ddd, J=8.2, 5.3 and 3.3 Hz, 1H). 19F-NMR (376 MHz, CDCl3): delta-116.9 (d, J=7.8 Hz, 1F), -116.3 (d, J=7.8 Hz, 1F).

The synthetic route of 399-94-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KAKEN PHARMACEUTICAL CO., LTD.; SAGAMI CHEMICAL RESEARCH INSTITUTE; KOBAYASHI, Osamu; NIIKURA, Naoko; INOUE, Tomoko; MIZUTA, Satoshi; TAKATSUNA, Reiko; HIRAI, Kenji; SHIROUZU, Kentaro; OBATA, Miyoo; (183 pag.)US2016/24110; (2016); 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. 4333-56-6, name is Bromocyclopropane, A new synthetic method of this compound is introduced below., Application In Synthesis of Bromocyclopropane

A solution of cyclopropyl bromide (22. 3 mL, 278 mmol) in diethyl ether (20 mL) was slowly added to a cooled suspension (0 C) of crushed lithium (5.8 g, 834 mmol) in ether (380 mL) (exothermic) under a nitrogen atmosphere. The reaction mixture was stirred for 90 minutes while the temperature rose to room temperature. The solution of this lithiate was slowly added to a cooled solution (0 C) ofN-methoxy-N-methyl-3, 3- [1, 2-ethanediylbis (oxy) ] estra- 5 (10), 9 (11), 16-triene-17-carboxamide (59.7 g, 139 mmol) in THF (260 mL). After stirring this mixture for 2 hours at 0 C, a saturated aqueous NILCl solution was added dropwise (exothermic) followed by water. The organic layer was separated and the aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried (Na2SO4) and evaporated to dryness. The crude product was purified by column chromatography (Si02, heptane/ethyl acetate, 4/1) to give 17- (cyclopropylcarbonyl) estra- 5 (10), 9 (11), 16-trien-3-one cyclic 1,2-ethanediyl acetal (33.9 g, 93 mmol, 67% yield).’H NMR (400 MHz, CDC13) : 8 0.82-2. 67 (m, 24H), 3.99 (s, 4H), 5.59 (m, 1H), 6.88 (m, 1H).

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; AKZO NOBEL N.V.; WO2005/92912; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 4333-56-6,Some common heterocyclic compound, 4333-56-6, name is Bromocyclopropane, molecular formula is C3H5Br, 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 30: (2S)-Lambda/-r(S)-cvclopropyl(phenyl)methvH-3-methyl-1 -f(trimethylsilyl)oxyl- 2-butanamine Cyclopropyl bromide (4.64g, 38.4mmole) was dissolved in dry diethyl ether (50ml) under argon, cooled to -780C and treated with tert-BuLi (45ml_ of a 1.7M solution in pentane, 76.5mmole). After 10 minutes, cooling was removed and the mixture stirred at room temperature for 1 hr. After re-cooling to -4O0C, a solution of Intermediate 28 (8.43g, 32mmole) in dry diethyl ether (40ml) was added and stirring continued at – 4O0C for 1.5 hrs. 5M HCI acid was added (50ml) and the phases separated. The aqueous phase was washed with diethyl ether (discarded) and then basified with KOH pellets to pH >10 in the presence of diethyl ether. The organic phase was washed with water and brine and then evaporated to dryness under vacuum to afford the title compound as a colourless oil (6.42g, 86%); 1 HNMR (400MHz, CDCI3): delta 0.13 – 0.15, (1 H, m), 0.34 – 0.37, (2H, m), 0.60 – 0.70, (1 H, m), 0.83, (3H, d, J = 7Hz), 0.91 , (3H, d, J = 7Hz), 0.98 – 1.00, (1 H, m), 1.71 – 1.77, (1 H, m), 2.44 – 2.48, (1 H, m), 3.00, (1 H, d, J = 8Hz), 3.32 and 3.36, (1 H, dd, J = 5 and 11 Hz), 3.59 and 3.61 , (1 H, dd, J = 5 and 11 Hz), 7.25 – 7.42, (5H, m); m/z(APCI): 234.2 [M+H]+.

The synthetic route of 4333-56-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/50991; (2006); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 55289-36-6, 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. 55289-36-6, name is 3-Bromo-2-methylaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a mixture of 3-bromo-2-methyl-aniline (10 g, 53.75 mmol) and 4,4,5,5-tetramethyl-2- (4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-l,3,2-dioxaborolane (27.30 g, 107.50 mmol) in dioxane (300 mL) were added KOAc (10.55 g, 107.50 mmol) and Pd(dppf)Cl2(3.93 g, 5.37 mmol) under N2.The mixture was stirred at 90 C for 12 h, and then concentrated. The residue was purified by flash silica gel chromatography (ISCO; 120 g SEP FLASH Silica Flash Column, Eluent of 0-15% Ethyl acetate/Petroleum ether gradient 100 mL/min) to give 2- methyl-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)aniline (8 g, 56.82% yield) as a yellow solid. LCMS: m/z found 234.2 [M+H]+.

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

Reference:
Patent; ARBUTUS BIOPHARMA, INC.; BI, Yingzhi; DORSEY, Bruce D.; FAN, Yi; MOORE, Christopher Brooks; NGUYEN, Duyan; (169 pag.)WO2019/191624; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

399-94-0, name is 1-Bromo-2,5-difluorobenzene, 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. Product Details of 399-94-0

Under nitrogen, 2,5-difluorobromobenzene (15.05 g, 78 mmol) was dissolved in dry toluene (50 mL)(66 mL, 1.3 mol / L) in an isopropylmagnesium chloride / lithium chloride solution was added dropwise to the temperature below -10 C, and the mixture was stirred at about -10 C for 1 hour. A solution of 1D (10 g, 39 mmol) in dry tetrahydrofuran (100 mL) was added dropwise to the reaction solution, maintaining the temperature at -10 C, and the reaction was carried out at room temperature for 4 hours. The temperature was reduced to about -10 C, and the saturated ammonium chloride solution (40 mL) was added dropwise. The mixture was stirred for 10 minutes. The pH was adjusted to 5 to 6 with 3 mol / L hydrochloric acid solution, (50 mL x 2). The organic phases were combined and washed with saturated sodium chloride solution (30 mL x 2). The organic phase was dried over anhydrous sodium sulfate, filtered, concentrated, and column chromatography (petroleum ether / Ethyl acetate (v / v) = 50: 1-8: 1),To give light yellow solid 1E (10.1 g, yield 83.5%).

The synthetic route of 399-94-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sichuan Haisco Pharmaceutical Co.,Ltd.; FAN, JIANG; ZHANG, CHEN; PENG, FEI; WU, YE; FENG, JIANCHUAN; WANG, JIANMIN; ZHENG, SUXIN; WEI, YONGGANG; YE, FEI; (350 pag.)TW2017/8220; (2017); A;,
Bromide – Wikipedia,
bromide – Wiktionary