Tag: M.W=100-200

Some common heterocyclic compound, 6775-78-6, name is 6-Chloroimidazo[1,2-b]pyridazine, molecular formula is C6H4ClN3, 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. Computed Properties of C6H4ClN3

Step 2: Preparation of 3-Bromo-6-chloroimidazo[1,2-b]pyridazine 478 mg (3.11 mmol) of 6-chloroimidazo[1,2-b]pyridazine were introduced into 10 mL of chloroform under argon and, while cooling in ice, 664 mg (3.73 mmol) of N-bromosuccuinimide were added. After the addition was complete, the reaction mixture was stirred at room temperature overnight. The reaction mixture was then mixed with water and ethyl acetate and, after addition of saturated sodium bicarbonate solution, the phases were separated. The aqueous phase was extracted three more times with ethyl acetate. The combined organic phases were then washed with sat. sodium chloride solution and dried over sodium sulfate. In the final removal of the solvent in vacuo, the desired product was isolated in quantitative yield in the form of an amorphous white solid which was employed without further chromatographic purification in subsequent reactions. 1H-NMR (CHLOROFORM-d): delta [ppm]=7.12 (1H); 7.79 (1H); 7.90 (1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6775-78-6, its application will become more common.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; Eis, Knut; Puehler, Florian; Zorn, Ludwig; Schulze, Volker; Suelzle, Detlev; Lienau, Philip; Haegebarth, Andrea; Petersen, Kirstin; Boemer, Ulf; US2015/87631; (2015); A1;,
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Reference of 57946-56-2,Some common heterocyclic compound, 57946-56-2, name is 4-Chloro-2-fluoroaniline, molecular formula is C6H5ClFN, 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 solution of 4-chloro-2-fluoroaniline (1.15 g, 7.9 mmol) in 125 mL of ethanol added silver sulphate (1.7 g, 8.3 mmol), then followed by addition of I2 (2.1 g, 8.3 mmol) in portions. After the addition was completed, the mixture was stirred at RT for 2 hours. The mixture was filtered through celite and the filtration was evaporated to give dark oil which was dissolved in 125 mL of DCM. The solution was washed with 2M sodium hydroxide (40 mL×2), saturated Na2S2O3 (40 mL×2) and water (40 mL×2). The resulting solution was dried over MgSO4 and then evaporated to give the crude 4-chloro-2-fluoro-6-iodoaniline as dark oil (2.1 g, yield: 98%).

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

Reference:
Patent; Hoffmann-La Roche Inc.; FENG, Song; GAO, LU; HONG, Di; WANG, Lisha; YUN, Hongying; ZHAO, Shu-Hai; (89 pag.)US2016/200741; (2016); A1;,
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Reference of 2687-12-9, 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. 2687-12-9 name is Cinnamyl chloride, This 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.

General procedure: A representative procedure of skeleton 4 is as follows: K2CO3 (400 mg, 2.9 mmol) was added to a solution of 3 (1.0 mmol) in acetone (10 mL) at rt. The reaction mixture was stirred at rt for 10 min. Cinnamyl chloride (1.05 mmol) was added to the reaction mixture at rt. The reaction mixture was stirred at reflux for 8 h. The reaction mixture was cooled to rt, concentrated, and extracted with CH2Cl2 (3×20 mL). The combined organic layers were washed with brine, dried, filtered, and evaporated to afford crude product under reduced pressure. Purification on silica gel (hexanes/EtOAc=6:1 to 1:1) afforded 4.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Cinnamyl chloride, and friends who are interested can also refer to it.

Reference:
Article; Chang, Meng-Yang; Lu, Yi-Ju; Cheng, Yu-Chieh; Tetrahedron; vol. 71; 8; (2015); p. 1192 – 1201;,
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Electric Literature of 2729-34-2, These common heterocyclic compound, 2729-34-2, name is 3,5-Dichloro-4-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.

To a cooled (-20 C) solution of (R)-2-tert-butoxycarbonylamino-propionic acid (57.2 g, 302 mmol) in anhydrous THF (582 mL) was added JV-methyl-morpholine (34.9 mL, 317 mmol) at a rate to keep the internal temperature at -15 C. Isobutyl chloroformate (42.0 mL, 317 mmol) was then added over a 20 min period and the resulting mixture was stirred for 30 min. A solution of 3,5-dichloro-4-fluoro-phenylamine (54.4 g, 302 mmol) in THF (160 mL) was then added over 40 min. The reaction mixture was warmed to 20 C and stirred for 20 h. The reaction mixture was filtered and concentrated in vacuo. To the resulting oil was added MeOH (200 mL) and the solution was concentrated to provide the title compound as a tan colored solid, m/z 295.3 [M-?-Bu]+. This material was used without further purification.

Statistics shows that 3,5-Dichloro-4-fluoroaniline is playing an increasingly important role. we look forward to future research findings about 2729-34-2.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2009/70485; (2009); A1;,
Chloride – Wikipedia,
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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. 13726-14-2, name is 4-Chloro-3-methoxyaniline, A new synthetic method of this compound is introduced below., category: chlorides-buliding-blocks

A mixture of substituted 2,4-dichloropyrimidine (1.0 equiv.), and substituted aniline (1.0-1.05 equiv.), and DIPEA (1.2 equiv.) in isopropanol (0.1 M) was stirred and heated at reflux. The reaction time, work-up, and product isolation procedure are described below. 2,5-Dichloro-/Y4-(4-chloro-3-methoxyphenyl)pyrimidin-4-amine (SG1-168): This was prepared from 2,4,5-trichloropyrimidine (0.500 g), 4-chloro-3-methoxyaniline (0.451 g), and DIPEA (0.570 mL) using procedure B (reaction time, 12 h). The solvent was removed and EtOAc (20 mL) was added. The organic layer was extracted with water (20 mL). The aqueous layer was re-extracted with EtOAc (20 mL). The organic layers were combined and washed with water and brine (20 mL each), dried (Na2S04) and concentrated under reduced pressure. The resulting dark purple oil was triturated using EtOAc/hexanes to give the title compound as a light purple solid (0.680 g, 82%). Mp: 136-138 C. NMR (400 MHz, DMSO-ifc): delta 9.57 (s, 1H, disappeared on D20 shake), 8.41 (s, 1H), 7.49 (d, / = 2.2 Hz, 1H), 7.41 (d, / = 8.6 Hz, 1H), 7.28 (dd, / = 8.6, 2.2 Hz, 1H), 3.82 (s, 3H). HPLC-MS (ESI+): m/z 308.1 [40%, (M35C137C137C1+H)+], 306.1 [98%, (M35C135C137C1+H)+], 304.0 [100%, (M35C135C135C1+H)+].

The synthetic route of 13726-14-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; H. LEE MOFFITT CANCER CENTER & RESEARCH INSTITUTE, INC.; SCHOeNBRUNN, Ernst; LAWRENCE, Nicholas J.; LAWRENCE, Harshani R.; (293 pag.)WO2017/66428; (2017); A1;,
Chloride – Wikipedia,
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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. 886762-39-6, name is 3,4-Dichloro-2-fluoroaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 3,4-Dichloro-2-fluoroaniline

1 .43 g of the compound obtained in (1-5), 1 .91 g of (R)-(-)-N-Boc-4- hydroxypiperidine and 1 .96 g of triphenylphosphine were added to 20 ml of methylene chloride, and 2.01 ml of diisopropylazodicarboxylate was added thereto dropwise. The resulting mixture was stirred at room temperature for 1 hour and distilled under a reduced pressure, and the residue was briefly purified by columnchromatography (ethylacetate : methylenechloride : methanol = 20 :20: 1). The partially purified residue was then dissolved in 60 ml of 2-propanol, 1 .17 g of 3,4- dichloro-4-fluoroaniline was thereto, and the mixture was stirred at 1 00 00 for 3 hours. The resulting mixture was distilled under a reduced pressure to remove the solvent, and the residue was dissolved in 60 ml of methylenechloride. 60 ml oftrifluoroacetic acid was added thereto and the mixture was stirred at room temperature for 1 hour. The resulting mixture was distilled under a reduced pressure to remove the solvent. Saturated sodium bicarbonate solution was added to the resulting residue to make it basic, followed by extraction with chloroform. The organic layer was dried over anhydrous sodium sulfate, filtered, and distilled under a reduced pressure. The resulting residue was subjected to column chromatography (chloroform : methanol = 1: 2) to obtain the title compound.

The synthetic route of 886762-39-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SPECTRUM PHARMACEUTICALS, INC.; CHATURVEDUAL, Prasad, V.; KOLLI, Prasad; (46 pag.)WO2019/79599; (2019); A1;,
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Synthetic Route of 363-51-9,Some common heterocyclic compound, 363-51-9, name is 2-Chloro-6-fluoroaniline, molecular formula is C6H5ClFN, 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: A Schlenk tube was charged with Oxone (0.398 g, 0.648mmol) and trifloroacetic acid (0.099 mL, 1.296 mmol) in anhydrous dioxane (2 mL) under argon. To this mixture was added 2-fluoroaniline (0.06 g, 0.54 mmol), and the reaction mixture was heated to 90 C under argon until starting material was consumed. As the reaction progressed, the color turned from lightred to dark red. The mixture was then cooled to room temperature and washed with a saturated aqueous sodium bicarbonate.The mixture was extracted with EtOAc (2 × 20 mL) and the combined organic layers were dried over Na2SO4. After filtering andremoval of the solvent under reduced pressure in vacuo, theresidue was purified by silica gel (100-200 mesh) column chromatography(hexane-EtOAc, 9:1), to afford a pale-brown solid(65%) of 2-hydroxy-N-trifluoroacetanilides from 2-fluoroaniline(2a).

The synthetic route of 363-51-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Venkateswarlu, Vunnam; Balgotra, Shilpi; Aravinda Kumar; Vishwakarma, Ram A.; Sawant, Sanghapal D.; Synlett; vol. 26; 9; (2015); p. 1258 – 1262;,
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Electric Literature of 870-24-6, 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. 870-24-6, name is 2-Chloroethanamine hydrochloride belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 3: Synthesis of t-butyl (2-chloroethyl)carbamate: 28.7 g (249 mmol) of 2-chloroethylamine hydrochloride was dissolved in 300 ml of dichloromethane. 41 g (192 mmol) of di-t-butyl dicarbonate and 80 ml (576 mmol) of triethylamine were added to the obtained solution, and they were stirred overnight. After the treatmentwith dichloromethane as the extraction solvent in an ordinary manner, the title compound was obtained. Yield: 41 g (229 mmol) (92 %) H-NMR (CDCl3) delta 1.43 (9H, s), 3.41 (2H, dt), 3.59 (2H, t), 4.95 (1H, br)

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, 2-Chloroethanamine hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Ajinomoto Co., Inc.; EP1065200; (2001); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 108-41-8, name is 1-Chloro-3-methylbenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: chlorides-buliding-blocks

General procedure: In the test tube were placed 7% Pd/WA30 (19.0 mg, 12.5 mumol), the aryl chloride (250 mumol), the arylboronic acid (375 mumol), Cs2CO3 (163 mg, 500 mumol), and DMA (1 mL). The mixture was stirred at 80 C under an Ar atmosphere. The reaction progress was monitored by TLC analysis (hexane-EtOAc, 5:1). When the reaction was completed within 24 h, the mixture was cooled to r.t., diluted with Et2O (5 mL), and passed through a cotton filter. The catalyst on the filter was washed with Et2O (2 × 15 mL) and H2O (3 × 10 mL). The combined filtrate was separated into two layers. The aqueous layer was extracted with Et2O (20 mL), and the combined organic layers were washed with H2O (4 × 20 mL) and brine (20 mL), dried over Na2SO4, filtered, and concentrated in vacuo. To the residue was added CDCl3 (ca. 1 mL) and 1,4-dioxane (8.53 muL, 100 mumol). After the determination of the reaction yield by 1H NMR, the product was purified by silicagel column chlomatography using hexane-EtOAc (10:1) as eluents to give the corresponding biaryl. When the reaction was incomplete after 24 h, the reaction mixture was treated in the same manner as described above.

The synthetic route of 108-41-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Monguchi, Yasunari; Ichikawa, Tomohiro; Netsu, Moeko; Hattori, Tomohiro; Mizusaki, Tomoteru; Sawama, Yoshinari; Sajiki, Hironao; Synlett; vol. 26; 14; (2015); p. 2014 – 2018;,
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These common heterocyclic compound, 2613-32-3, name is 2-Chloro-4,5-difluoroaniline, 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. name: 2-Chloro-4,5-difluoroaniline

1-Chlor-1-dimethylamino-2-methyl-1-propen (64.9 mg, 0.486 mmol) was added to a solution of trans-4-[(pyrazolo[1 ,5-a]pyrim idin-3-ylcarbonyl)am ino]cyclohexanecarboxylic acid (70.0 mg, 0.243 mmol) in dichloromethane (3.1 ml) and the mixture was stirred at roomtemperature for 30 mi Pyridine (59 p1, 0.0.73 mmol) and 2-chloro-4,5-difluoroaniline (39.7 mg, 0.243 mmol, GAS No 261 3-32-3) were added and the mixture was stirred over night at room temperature. For work-up, water was added and the reaction mixture was extracted with dichloromethane. Die organic phase was filtrated through a silicone filter, concentrated and the residue purified by preparative HPLG (Method 9) to yield the title compound (3.8 mg,4% yield).LG-MS (Method 2): R = 1 .10 mm; MS (ESIpos) m/z = 434.1 [M+H].1HNMR (400 MHz, DMSO-d6): 6 [ppm] = 9.62 (5, 1H), 9.32 (dd, 1H), 8.83 (dd, 1H), 8.58 (5,1H), 7.86-7.76 (m, 3H), 7.28 (dd, 1H), 3.90-3.76 (m, 1H), 2.12-1.91 (m, 4H), 1.66-1.50 (m,2H), 1.45-1.31 (m, 2H).

The synthetic route of 2-Chloro-4,5-difluoroaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; EIS, Knut; ACKERMANN, Jens; WAGNER, Sarah; BUCHGRABER, Philipp; SUeLZLE, Detlev; HOLTON, Simon; BENDER, Eckhard; LI, Volkhart; LIU, Ningshu; SIEGEL, Franziska; LIENAU, Philip; BAIRLEIN, Michaela; VON NUSSBAUM, Franz; HERBERT,Simon; KOPPITZ, Marcus; (734 pag.)WO2016/177658; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics