Category: 766-11-0

Electric Literature of 766-11-0 , The common heterocyclic compound, 766-11-0, name is 5-Bromo-2-fluoropyridine, molecular formula is C5H3BrFN, 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 stirred solution of 5-bromo-2-fluoro-pyridine (10.0 g, 56.82 mmol) in ethanol (120 mL) was added hydrazine hydrate (11.38 g, 227 mmol) and heated to 80 C for 12 hours The reaction mixture was cooled to room temperature and treated with ice water (200 mL). The precipitated solid was filtered, washed with water and dried to get the product (10.7 g) as a solid. It was used for the next step without further purification.

The synthetic route of 766-11-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PRAXIS PRECISION MEDICINES, INC.; GRIFFIN, Andrew, Mark; MARRON, Brian, Edward; MARTINEZ BOTELLA, Gabriel; REDDY, Kiran; WITTMANN, Marion; (0 pag.)WO2019/232209; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

766-11-0 , The common heterocyclic compound, 766-11-0, name is 5-Bromo-2-fluoropyridine, molecular formula is C5H3BrFN, 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.

Example 51; 4-[{2-[(6-Fluoro-3-pyridinyl)oxy]ethyl}(2,2,2-trifluoroethyl)amino]-2- (trifluoromethyl)benzonitrile; A. 6-Fluoro-3-pyridinol; To a solution of 5-bromo-2-fluoropyridine (0.26 mL, 2.5 mmol) in dry Et2O (10 mL) at -78C was added n-BuLi (1.06 mL of a 2.5 M solution in hexanes, 2.7 mmol), dropwise over 3 min. The mixture was stirred 15 min and B(O/-Pr)3 (0.64 mL, 2.8 mmol) was added dropwise. The mixture was gradually warmed to rt over 30 min, 1 M NaOH (2 mL) was added, followed by H2O2 (0.5 mL of a 30 wt% solution) and the mixture was stirred 30 min. Excess H2O2 was quenched by dropwise addition of a 10% solution of Na2S2O3, the mixture was poured into water and the layers were separated. The aqueous layer was adjusted to pH 3.5 by addition of 1M KHSO4 and extracted with EtOAc (x3). Combined organics portions were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/hexanes), affording 0.242 g of the title compound as a colorless solid: MS (APCI) m/z 114 (M+H).

The synthetic route of 766-11-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/44707; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

766-11-0, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 766-11-0, name is 5-Bromo-2-fluoropyridine. This compound has unique chemical properties. The synthetic route is as follows.

Example D-1 : Preparation of (2S)-1-(4-(1-isopropyl-3-(1H-pyrazolo[3,4-b]pyridin-5-yl)-1H-pyrazol-4- yl)pyrimidin-2-ylamino)propan-2-ol -J B-B; i/Pd(PPh3)2CI2, KOAc, DMF Preparation of 5-bromo-2-fluoronicotinaldehyde (D-1-2).D-1-1 D-1-2To a solution of diisopropylamine (17 mL, 0.17 mol) in dry THF (200 mL) was added 2.5 M n-BuLi in hexane (68 mL, 0.17 mol) dropwise at O 0C under N2 atmosphere. After the addition, the resulting mixture was cooled to -65C. A solution of 5-bromo-2-fluoropyridine (25 g, 0.14 mol) in dry THF (100 mL) was then added dropwise. The resulting mixture was stirred at -65C for 90 minutes. Then ethyl formate (15.6 g, 0.21 mol) was added dropwise to the mixture. After stirred for 10 minutes, the reaction mixture was quenched with a solution of 10% citric acid in THF (100 mL) at -650C. The resulting mixture was warmed up to room temperature, poured into water (100 mL) and extracted with EtOAc (200 mL). The organic layer was separated and washed with saturated aqueous NaCI (100 mLchi2), dried over Na2SO4 and concentrated in vacuo to yield compound D-1-2 (25 g, 85%) as a yellow solid.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 766-11-0, 5-Bromo-2-fluoropyridine.

Reference:
Patent; PFIZER INC.; WO2009/16460; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

766-11-0, A common compound: 766-11-0, name is 5-Bromo-2-fluoropyridine,molecular formula is C5H3BrFN, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Preparation of 3-Methyl-5-(4,4,5,5-tetramethyl-[1 ,3,2]dioxaborolan-2-yl)-1 H-pyrazolo[3,4-b]pyridine (79) 7475 76 77Step 1 :7475To a stirred solution of diisopropyl-amine (50 g, 0.5 mol) in dry THF (1000 mL) was added dropwise n- BuLi (200 mL, 0.5 mol) at -780C under N2 atmosphere. After the addition, the resulting mixture was allowed to warm up to O0C, maintained for 10 minutes and cooled to -780C again. A mixture of compound 74 (80 g, 0.455 mol) in THF (1000 mL) was added dropwise to the LDA solution at -780C under N2 atmosphere. After the addition, the reaction mixture was stirred at -780C for 30 minutes. Then formic acid ethyl ester (50 g, 0.68 mol) was added portionwise to the mixture at -780C. After 2 minutes, the resulting mixture was quenched with a solution of 10% citric acid in THF (400 mL) at -780C. The mixture was allowed to warmed up to room temperature and poured into H2O (500 mL), extracted with EtOAc (500 mL x 3). The combined organic layers were washed with brine (500 mL), dried over Na2SO4 and concentrated in vacuo to give compound 75 (92 g, 99%) as a yellow solid.

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 766-11-0.

Reference:
Patent; PFIZER INC.; WO2009/16460; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

766-11-0, 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. 766-11-0, name is 5-Bromo-2-fluoropyridine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of alcohol 1a-r or benzyl mercaptan 1s (1.5 equiv.) in anhydrous THF (100 mL) was slowly added 60% sodium hydride (2.0 equiv.). The mixture was allowed to react at room temperature for 30 min then it was heated to reflux for 1 h. 5-bromo-2-fluoropyridine (1 equiv.) was added and the reaction was continued for 12 h. After cooling down to room temperature, the mixture was poured into water and extracted with ethyl acetate. The organic phase was washed with brine, dried on MgSO4, filtered, evaporated and purified by silica gel chromatography.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 766-11-0, 5-Bromo-2-fluoropyridine.

Reference:
Article; Fontaine, Fanny; Hequet, Arnaud; Voisin-Chiret, Anne-Sophie; Bouillon, Alexandre; Lesnard, Aurelien; Cresteil, Thierry; Jolivalt, Claude; Rault, Sylvain; European Journal of Medicinal Chemistry; vol. 95; (2015); p. 185 – 198;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 766-11-0, name is 5-Bromo-2-fluoropyridine, molecular formula is C5H3BrFN, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. 766-11-0

Step 1: Synthesis of 5-bromo-2-fluoro-pyridine-3-carbaldehyde.[0217] A solution of lithium di-zso-propylamine (5 mL, 35 mmol) in anhydrous THF (40mL) was cooled to -78 C under nitrogen and n-butyl lithium (2.5 M in hexanes, 12 mL, 30mmol) was added. The mixture was then stirred at -78 C for 15 min before 5-bromo-2-fluoro-pyridine (5 g, 28 mmol) was added. The resulting mixture was then stirred at -78 Cfor 90 min. 7V-formylpiperidine (4 mL, 36 mmol) was added very rapidly to the suspensionat -78 C and the mixture stirred vigorously for 60 sec. The reaction was immediately quenched by the addition of a 10 % (w/v) aqueous solution of citric acid. The mixture waswarmed to room temperature and distributed between water and dichloromethane. Theaqueous phase was extracted three times with dichloromethane and the organic phases werecombined, dried over sodium sulfate, filtered and concentrated. Crystallization of the crudeproduct from cyclohexane afforded 5-bromo-2-fluoro-pyridine-3-carbaldehyde (2.993 g,52% yield) as pale beige flaky crystals.

The chemical industry reduces the impact on the environment during synthesis 766-11-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; SGX PHARMACEUTICALS, INC.; WO2006/15124; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

766-11-0, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 766-11-0, name is 5-Bromo-2-fluoropyridine. This compound has unique chemical properties. The synthetic route is as follows.

A solution of lithium di-iso-propylamine (5 mL, 35 mmol) in anhydrous THF (40 mL) was cooled to -78 C. under nitrogen and n-butyl lithium (2.5 M in hexanes, 12 mL, 30 mmol) was added. The mixture was then stirred at -78 C. for 15 min before 5-bromo-2-fluoro-pyridine (5 g, 28 mmol) was added. The resulting mixture was then stirred at -78 C. for 90 min. N-formylpiperidine (4 mL, 36 mmol) was added very rapidly to the suspension at -78 C. and the mixture stirred vigorously for 60 sec. The reaction was immediately quenched by the addition of a 10% (w/v) aqueous solution of citric acid. The mixture was warmed to room temperature and distributed between water and dichloromethane. The aqueous phase was extracted three times with dichloromethane and the organic phases were combined, dried over sodium sulfate, filtered and concentrated. Crystallization of the crude product from cyclohexane afforded 5-bromo-2-fluoro-pyridine-3-carbaldehyde (2.993 g, 52% yield) as pale beige flaky crystals. 1H-NMR (500 MHz, d6-DMSO) delta 10.07 (s, 1H), 8.70 (dd, 1H), 8.55 (dd, 1H). MS: m/z 236, 238 [MNa+], 204, 206 [MH+], 176, 178 [MH-CO+].

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 766-11-0, 5-Bromo-2-fluoropyridine.

Reference:
Patent; SGX Pharmaceuticals, Inc.; US2008/261921; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem