Chlorides-buliding-blocks

Application of 13918-92-8,Some common heterocyclic compound, 13918-92-8, name is 2,4-Difluorobenzene-1-sulfonyl chloride, molecular formula is C6H3ClF2O2S, 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.

N-[5-Bromo-2-(methyloxy)-3-pyridinyl]-2,4-difluorobenzenesulfonamide To a cooled (0 C.) solution of 5-bromo-2-(methyloxy)-3-pyridinamine (13.7 g, 67.5 mmol) in pyridine (200 ml) was added slowly 2,4-difluorobenzenesulfonyl chloride (14.37 g, 67.6 mmol) over 15 min (reaction became heterogeneous). The ice bath was removed and the reaction was stirred at ambient temperature for 16 h. Most of the pyridine was removed in vacuo and the residue diluted with water (500 mL). The solids were filtered off and washed with copious amounts of water to give 21 g of crude desired product. More solid appeared in the mother liquor and was filtered and washed with water to give an additional 1.5 g of desired material. The two batches were combined, triturated with 70 ml of methylene chloride, and dried in a vacuum oven at 50 C. to give the title compound (15 LCMS (Method B) R=1.1 1 mi MH=378/380.

The synthetic route of 13918-92-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Glaxo Group Limited; Hamblin, Julie Nicole; Jones, Paul Spencer; Keeling, Suzanne Elaine; Le, Joelle; Mitchell, Charlotte Jane; Parr, Nigel James; (136 pag.)US9326987; (2016); B2;,
Chloride – Wikipedia,
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Synthetic Route of 38762-41-3, 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. 38762-41-3, name is 4-Bromo-2-chloroaniline, This compound has unique chemical properties. The synthetic route is as follows.

To toluene (1470 mL) and water (60 mL) under nitrogen was added 4-bromo-2-chloroaniline (63 g, 305 mmol) and cyclopropylboronic acid (26.5 g, 309 mmol). The mixture was cooled and treated with potassium phosphate tribasic (227 g, 1068 mmol) portionwise followed by P(cHex)3 (8.56 g, 30.5 mmol). The flask was flushed with nitrogen, Pd(OAc)2 (3.56 g, 15.87 mmol) was added and the mixture was heated to 81 C. for 7 hrs then left at RT over the weekend. Further cyclopropylboronic acid (5.5 g, 64 mmol) was added and the mixture was heated to 81 C. for 2 hrs and then cooled to RT. The resulting mixture was diluted with water (600 mL). The aqueous layer was separated and the organic layer was washed with water (300 mL) and brine (300 mL), dried over Na2SO4, filtered and evaporated to dryness to give a brown oil. The oil was absorbed onto silica and purified by chromatography eluting with 10-100% EtOAc in heptane. The product fractions were combined and concentrated under reduced pressure to give the title compound as green crystals. (0513) HPLC Method D: Rt 3.94 mins; (0514) 1H NMR (400 MHz, DMSO-d6) delta 6.88 (1H, d), 6.74 (1H, dd), 6.67 (1H, d), 5.06 (2H, br s), 1.78-1.70 (1H, mult), 0.82-0.76 (2H, mults), 0.52-0.47 (2H, mults).

The chemical industry reduces the impact on the environment during synthesis 4-Bromo-2-chloroaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; NOVARTIS AG; EDWARDS, Anne-Marie; AHMED, Mahbub; PULZ, Robert Alexander; ROONEY, Lisa Ann; SMITH, Nichola; TROXLER, Thomas Josef; (31 pag.)US2015/329549; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 62593-17-3, name is 2,4-Dichloro-6-(trifluoromethyl)aniline, belongs to chlorides-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 62593-17-3, Product Details of 62593-17-3

2,4-Dichloro-6-trifluoromethylphenylacetic acid methyl ester prepared from 2,4-dichloro-6-trifluoromethylaniline; LC-MS (A): tR=0.93 min; 1H NMR ((CD3)2SO) delta: 8.11 (s, 1H), 7.88 (s, 1H), 3.97 (s, 2H), 3.65 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,4-Dichloro-6-(trifluoromethyl)aniline, and friends who are interested can also refer to it.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD.; Hilpert, Kurt; Hubler, Francis; Kimmerlin, Thierry; Renneberg, Dorte; Stamm, Simon; Murphy, Mark; US2014/163035; (2014); A1;,
Chloride – Wikipedia,
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2106-04-9, name is 3-Chloro-2-fluoroaniline, belongs to chlorides-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 2106-04-9

To a mixture of 3-chloro-2-fluoroaniline (18.0 g, 124 mmol) in MeCN (100 mL) was added a solution of NBS (26.4 g, 148 mmol) in MeCN (100 mL) in a dropwise manner at 25 C. The mixture was stirred at 25 C for 4 h. The reaction mixture was concentrated in vacuo to give the crude product. The crude material was purified by silica-gel column chromatography (petroleum ether/EtOAc, 50:1) to give 4-bromo-3-chloro-2-fluoroaniline as a brown oil (18.0 g, yield: 65%). 1H NMR: (400 MHz, CD3OD) d: 7.13 (dd, J2 = 8.8 Hz, J2 = 2.0 Hz, 1H), 6.66 (t, / = 8.4 Hz, 1H).

The synthetic route of 2106-04-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOGEN MA INC.; HOPKINS, Brian, T.; MA, Bin; PRINCE, Robin; MARX, Isaac; SCHULZ, Juergen; NEVALAINEN, Marta; DECHANTSREITER, Michael; (273 pag.)WO2019/222101; (2019); A1;,
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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. 13078-79-0, name is 2-(3-Chlorophenyl)ethanamine, A new synthetic method of this compound is introduced below., Product Details of 13078-79-0

General procedure: NaBH(OAc)3 (3 eq) was added to an ethanol solution (15 mL)of the aldehyde 9 (1 g) and alkylamines (2 eq), and the mixture was stirred for 4 h at 0 to room temperature. After completionof the reaction, the reaction mixture was evaporated under reduced pressure to give a crude residue, which was purified by asilica gel (300-400 mesh) column using petroleum ether/ethyl acetate (5:1?2:1) to obtain pure compound 10a-i.

The synthetic route of 13078-79-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Haibo; Pan, Yang; Tang, Qin; Zou, Wei; Shao, Huawu; Chinese Chemical Letters; vol. 29; 1; (2018); p. 73 – 75;,
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Electric Literature of 2106-02-7, 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. 2106-02-7, name is 2-Chloro-4-fluoroaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Lithium hexamethyldisilazide (22.9 ml, 22.9 mmol, 1 M solution in tetrahydrofuran) was added over 5 min to solution of 2-chloro-4-fluoroaniline (1 .84 g, 12.6 mmol, Cas No 2106-02-7) in tetrahydrofuran (60 ml) at -78 and the mixture was stired at -78 for 1 h. A solution of ethyl 4-{[tert-butyl(dimethyl)silyl]oxy}-1-(2-chloroethyl)cyclohexanecarboxylate (mixture of cis-/trans-isomers) (4.00 g, 1 1 .5 mmol) in tetrahydrofuran (60 ml) was added and the mixture was stirred for 2 h at -78 and the for 3 days at room temperature. For work-up, the reaction mixture was poured into a mixture of water and saturated sodium bicarbonate solution, extracteted with ethyl acetate (3x) and the combined organic phases were washed with brine, filtrated through a silicone filter and concentrated under reduced pressured. The residue was purified by flash chromatography (Snap Cartdidge, hexanes/ethyl acetate gradient) to give 8-{[tert-butyl(dimethyl)silyl]oxy}-2-(2-chloro-4-f luorophenyl)-2-azaspiro[4.5]decan-1-one in 2 fractions. Fraction 1 (1 .88 g, isomer 1, contains ca 20mol% 2-chloro-4-fluoroaniline) and fraction 2 (485 mg, isomer 2).Fraction 1 (isomer 1 ):LC-MS (Method 1 ): Rt= 1 .68 min; MS (ESIpos) m/z = 412.2 [M+H]+.1H-NMR (400 MHz, DMSO-d6): delta [ppm] = 7.58 (dd, 1H), 7.46 (dd, 1H), 7.30 (td, 1H), 3.97-3.92 (m, 1H), 3.59 (t, 2H), 2.06 (t, 2H), 2.01-1 .92 (m, 2H), 1.71-1.54 (m, 4H), 1 .36-1 .29 (m, 2H), 0.92-0.86 (m, 9H), 0.08-0.03 (m, 6H).Fraction 2 (isomer 2):LC-MS (Method 1 ): Rt= 1 .67 min; MS (ESIpos) m/z = 412.2 [M+H]+.1H-NMR (400 MHz, DMSO-d6): delta [ppm] = 7.57 (dd, 1H), 7.45 (dd, 1H), 7.33-7.25 (m, 1H), 3.70-3.52 (m, 3H), 2.07 (t, 2H), 1 .84-1 .74 (m, 2H), 1.62-1 .54 (m, 4H), 1 .42-1.28 (m, 2H), 0.89-0.83 (m, 9H), 0.07-0.01 (m, 6H)

The synthetic route of 2-Chloro-4-fluoroaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BUCHGRABER, Philipp; EIS, Knut; WAGNER, Sarah; SUeLZLE, Detlev; VON NUSSBAUM, Franz; BENDER, Eckhard; LI, Volkhart, Min-Jian; LIU, Ningshu; SIEGEL, Franziska; LIENAU, Philipp; (248 pag.)WO2018/78005; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 771583-81-4, These common heterocyclic compound, 771583-81-4, name is 4-Chloro-2-(trifluoromethyl)benzylamine, 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.

5-((4- (ethylsulfonyl) benzyl) carbamoyl) -2-fluorobenzoic acid (150.0 mg, 0.4 mmol), HATU (234.0 mg, 0.6 mmol), and DIPEA (211.8 mg, 1.6 mmol) ) Dissolved in tetrahydrofuran (10mL), stirred at room temperature for 0.5 hours, then added 4-chloro-2- (trifluoromethyl) benzylamine (129.1mg, 0.6mmol), reacted at room temperature for 4 hours, then added an appropriate amount Water and extracted three times with ethyl acetate. The organic phases were combined and washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The concentrate was purified by preparative high performance liquid chromatography to obtain the title compound (100.0 mg, yield: 42%).

The synthetic route of 771583-81-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sichuan Kelun Botai Bio-pharmaceutical Co., Ltd.; Liu Chunchi; Liu Jinming; Ren Yun; Cai Jiaqiang; Wang Lichun; Wang Jingyi; (42 pag.)CN110724075; (2020); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 102-49-8,Some common heterocyclic compound, 102-49-8, name is 3,4-Dichlorobenzylamine, molecular formula is C7H7Cl2N, 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 solution of acid 4 (0.09 g, 0.47 mmol) in dry DMF (2 mL) treated sequentially with amine (5a?i, 6a?e and 7a?h; 0.517 mmol)and triethylamine (0.94 mmol) was stirred under a N2 atmosphere for 15 min, later TBTU (0.56 mmol) was added and reaction mixture refluxed for 4?10 h. The reaction mixture was quenched with aq satd NH4Cl solution (10 mL). After 10 min, it was diluted withCHCl3 (2 10 mL) and washed with water (10 mL), NaHCO3 solution(10 mL) and brine (10 mL). The organic layers were dried over anhydrous sodium sulfate, evaporated and the residue purified by column chromatography using 30percent ethyl acetate in pet. ether to afford corresponding amides 8a?i, 9a?e and 10a?h.

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

Reference:
Article; Doma, Anuradha; Kulkarni, Ravindra; Palakodety, Radhakrishna; Sastry, G. Narahari; Sridhara, Janardhan; Garlapati, Achaiah; Bioorganic and Medicinal Chemistry; vol. 22; 21; (2014); p. 6209 – 6219;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 461432-23-5, name is 4-Bromo-1-chloro-2-(4-ethoxybenzyl)benzene, belongs to chlorides-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 461432-23-5, category: chlorides-buliding-blocks

To the mixture of 10 cc THF and 10 cc Toluene added 0.138 mole 4-(5-bromo-2- chlorobenzyl)phenyl ethyl ether at ambient temperature and stirred for 15 min. Cooled to -70 to -80C in dry ice /acetone bath and stirred for 15 min. Added a solution of 0.014 mole n-Butyl lithium (1.9M in hexanes) at -70 to -80C. and stirred for lhr. Added solution of 3, 4, 5-Tris-trimethylsilanyloxy-6-trimethylsilanyloxymethyl-tetrahydro- pyran-2-one in 5 cc of Toluene at -70 to -80C and stirred for 2 to 3hrs. After the compliance of the reaction, reaction mass was quenched with Methane sulphonic acid and Allyl alcohol mixture at -70 to -80C. Temperature was raised to ambient temperature and stirred overnight. Reaction mass was quenched with 30 cc sat.sodiumbicarbonate solution to bring the pH neutral to alkaline and stirred for 30.0 min. Layers separated and aqueous layer was extracted with 10 cc of Toluene. Organic layer was combined and washed with 30cc water and 50 cc sat. brine solution. Organic layer was distilled under reduced pressure to recover toluene. Solid compound was dissolved in 50cc of toluene and quenched in n-Hexane to obtain 83 % the compound as crystalline solid. HPLC purity: 88 – 91 % I R data: Anomeric C-0 stretching: 1242 cm”1 Allylic C- O stretching: 1 177 cm”1 Allylic C- H stretching: 3010 – 3120 cm”1 Aromatic C- CI stretching: 820 cm”1 Lactones O – H stretching: 3240 – 3380 cm”1 Lactones C – 0 stretching: 1045 – 1092 cm”1 Aromatic C=C stretching: 1510 , 1548 , 1603 , 1703 cm”1 Alkane C – H stretching: 2877,2866, 2956, 2958, 2962 cm”1 Aromatic C – H stretching: 3050 – 3090 cm”1 Dip-Mass (M+Na) 487.19 m/z (M+K) 503.17 m/z

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-1-chloro-2-(4-ethoxybenzyl)benzene, and friends who are interested can also refer to it.

Reference:
Patent; HARMAN FINOCHEM LIMITED; KADAM, Vijay Trimbak; SAIKRISHNA; CHOUDHARE, Tukaram Sarjerao; MINHAS, Harpreet Singh; MINHAS, Gurpreet Singh; (26 pag.)WO2016/147197; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 918538-05-3, name is 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine, molecular formula is C6H3Cl2N3, 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. COA of Formula: C6H3Cl2N3

To a 100 mL flask was added 2,4-dichloropyrrolo[2,l-^[l,2,4]triazine (3 g, 15.96 mmol), tetrahydrofuran (40 mL) and stirred. To the resulting solution was portionwise added sodium phenolate (2.038 g, 17.55 mmol). After 1 h, an aliquot of the reaction mixture was diluted with methanol and anlayzed by LCMS to ensure complete conversion. The reaction mixture was concentrated. To the residue was added water, stirred, filtered and dried. Obtained 2-chloro-4-phenoxypyrrolo[2,l- |[l,2,4]triazine (3.71 g, 15.10 mmol, 95 % yield) as an off-white solid. LCMS: RT = 1.05 min; MS(ES): m/z observed = 245.9, 247.9 (Injection conditions: Column: Waters Acquity UPLC BEH C18, 2.1 x 50 mm, 1.7-muiotaeta particles; Mobile Phase A: 100% water with 0.05% TFA; Mobile Phase B: 100% MeCN with 0.05% TFA; Gradient: 2-98% B over 1 minute, then a 0.5- minute hold at 98% B; Flow: 0.8 mL/min; Detection: UV at 220 nm); NMR (300 MHz, DMSO-de) delta 8.13 (dd, J=2.6, 1.5 Hz, 1H), 7.56 – 7.48 (m, 2H), 7.42 – 7.34 (m, 3H), 7.15 (dd, J=4.5, 1.5 Hz, 1H), 6.99 (dd, J=4.5, 2.6 Hz, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 918538-05-3, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BORZILLERI, Robert M.; FINK, Brian E.; HARIKRISHNAN, Lalgudi S.; WARRIER, Jayakumar Sankara; (87 pag.)WO2017/40448; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics