Ethers-buliding-blocks

Adding a certain compound to certain chemical reactions, such as: 29578-39-0, name is 1-Bromo-3-fluoro-5-methoxybenzene, belongs to ethers-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 29578-39-0, category: ethers-buliding-blocks

A solution of 1 -(4-(3,4-dichlorophenyl)-5-(isopropylthio)thiazol-2-yl)-5- (methoxycarbonyl)-3-methyl-1 H-pyrazol-4-ylboronic acid (41 mg, 0.083 mmol), 1-bromo-3- fluoro-5-methoxybenzene (20 mg, 0.10 mmol), Pd(PPh3)4 (10 mg, 0.0083 mmol), Na2003 (44 mg, 0.42 mmol) in degassed 1,4-dioxane and H20 (4:1, 1.7 mL) was heated at 85 C for 18 hours. LiOH (10 mg, 0.42 mmol) was added and the reaction was heated at 95 O under microwave radiation for 30 mm. i N HCI (1 mL) was added, followed by water (5 mL) and the mixture was extracted with EtOAc (3x5mL). The combined organic layers were dried with sodium sulfate, filtered and evaporated under reduced pressure. The crude product was purified by semi-prep H PLC-MS (column X-Bridge 30×50) using a solution of MeCN in water (containing 10 mM of ammonium formate) (60 to 80%). The product was lyophylised to give the title compound (16 mg, 0.028 mmol, 34%) as a pale yellow solid. 1H NMR (500 MHz, DMSO) O 8.21 (d, J= 1.8 Hz, 1H), 8.03 (dd, J= 8.5, 1.8 Hz, 1 H), 7.75 (d, J = 8.5 Hz, 1 H), 6.94 -6.89 (m, 2H), 6.86 (d, J = 11.5 Hz, 1 H), 3.80 (5, 3H),3.35 (sept, J = 6.7 Hz, 1H), 2.32 (5, 3H), 1.24 (d, J= 6.7 Hz, 6H); MS (mlz): 552.1 [M+1].

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, 1-Bromo-3-fluoro-5-methoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BANTAM PHARMACEUTICAL, LLC; SIDDIQUI, M. Arshad; CIBLAT, Stephane; CONSTANTINEAU-FORGET, Lea; GRAND-MAITRE, Chantal; GUO, Xiangyu, Jr.; SRIVASTAVA, Sanjay; SHIPPS, Gerald W.; COOPER, Alan B.; OZA, Vibha; KOSTURA, Matthew; LUTHER, Michael; LEVINE, Jedd; (253 pag.)WO2018/102452; (2018); A2;,
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In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 145903-31-7 as follows. Safety of 7-Methoxy-2,3,4,5-tetrahydrobenzo[f][1,4]thiazepine

Experimental Example 4 7-Methoxy-2,3,4,5-tetrahydro-1,4-benzothiazepine (3.0 g), triethylamine (3.1 g) and bromoacetyl chloride (3.2 g) were reacted in the same manner as in Experimental Example 1 to give 4-bromoacetyl-7-methoxy-2,3,4,5-tetrahydro-1,4-benzothiazepine (2.5 g). IR numaxCHCl3 (cm-1): 1640 1 H-NMR(CDCl3, 100 MHz)delta: 2.75-2.94 (2H, m), 3.68-4.18 (4H, m), 3.80 (3H, s), 4.66-4.81 (2H, m), 6.65-7.58 (3H, m).

According to the analysis of related databases, 145903-31-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kirin Brewery Co., Ltd.; US5416066; (1995); A;,
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Reference of 366-99-4, 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. 366-99-4, name is 3-Fluoro-4-methoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 4a (see general route 4, procedure H, M and K)2-(3-fluoro-4-methoxyphenyl)hydrazine; [00257] A room temperature solution of 3-fluoro-4-methoxyaniline (25.0 g, 177 mmol) in concentrated 12M aqueous hydrochloric acid solution (60 mL) was stirred for two hours, after which it was cooled to 0°C to which a solution of sodium nitrite (14.2 g, 205 mmol), in water (50 mL), was added, drop-wise over 45 minutes, with internal temperature monitoring such that the reaction temperature does not warm above 5°C. After stirring for one hour at 0°C, the reaction mixture was poured slowly into a 0°C pre-made solution of tin(II) chloride dihydrate (168 g, 744 mmol) in concentrated 12M aqueous hydrochloric acid solution (125 mL). The reaction mixture was allowed to warm up to room temperature, after which it was stored in the freezer overnight (12 hours), leading to the formation of a precipitate. This dark brown solid was successively washed with water (2 x 100 mL) and diethyl ether (3 x 100 mL), and dried to afford crude 2-(3-fluoro-4-methoxyphenyl)hydrazine hydrochloride as a pasty brown solid (note that this crude solid can also be used directly in the next step). As part of the purification and isolation process, the crude hydrazine hydrochloride salt was reconstituted in water (100 mL) and 3M aqueous sodium hydroxide solution (200 mL), extracted with diethyl ether (2 x 200 mL), washed with successively with saturated sodium bicarbonate solution (2 x 100 mL), water (2 x 20 mL) and saturated sodium chloride solution (2 x 20 mL), dried (sodium sulfate), filtered and concentrated to afford 2-(3-fluoro-4- methoxyphenyl)hydrazine as a light yellow solid (15.0 g, 96.1 mmol, 54percent yield. 1H NMR (400 MHz, CDC13) delta (ppm): 6.87 (m, 1H), 6.66 (dd, 1H), 6.49-6.53 (m, 1H), 5.06 (br. s, 1H), 3.83 (s, 3H), 3.55 (br. s, 2H).[00258] A portion of 2-(3-fluoro-4-methoxyphenyl)hydrazine (5.00 g, 32.0 mmol) was dissolved in absolute ethanol (50 mL), to which a solution hydrogen chloride (15 mL, 2.5M in ethanol) was added. The resulting precipitate was filtered, washed with ethyl acetate (2 x 40 mL), and dried to afford 2-(3-fluoro-4-methoxyphenyl)hydrazine hydrochloride as an off- white solid (4.7 g).

The synthetic route of 3-Fluoro-4-methoxyaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRONWOOD PHARMACEUTICALS, INC.; HUDSON, Colleen; BARDEN, Timothy, C.; JIA, James; MERMERIAN, Ara; PENG, Bo; YANG, Jane; YU, Xiang, Y.; SPROTT, Kevin; WO2012/88469; (2012); A1;,
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Reference of 112970-44-2, 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. 112970-44-2 name is 2-Bromo-3-methoxyaniline, 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.

A dry round-bottom flask with a reflux condenser was charged with 2-bromo-3-methoxyanilin (1.00 g, 4.95 mmol), KHMDS(32 mg, 0.16 mmol, 0.03 eq), BrettPhos Pd G1 Methyl-t-Butyl Ether adduct (118 mg, 0.15 mmol, 0.03 eq) and Cs2CO3 (3.22 g,9.88 mmol, 2.0 eq). The system was sealed by a rubber septum before air was removed under reduced pressure and replaced by argon (repeated 3 times). Anhydrous toluene (20 mL) was transferred to the flask and the resulting orange colored suspension gradually warmed up to reflux and left stirring for 24 h. The heating was removed and the crude mixture was cooled to reach rt . Thereaction mixture was filtered through a funnel of Celite and undissolved material washed with DCM until no yellow solution came through the funnel. The resulting crude mixture was dry-loadedon silica and purified by flash column chromatography on silicagel (1:7 EtOAc/DCM as eluent) affording 468 mg (79%) of the yellow solid. Rf: 0.51 (100% EtOAc). 1H NMR (400 MHz, CDCl3) d7.99 (dd, J = 8.9, 1.1 Hz, 2H), 7.74 (dd, J = 8.9, 7.6 Hz, 2H), 7.09(dd, J = 7.6, 1.1 Hz, 2H), 4.17 (s, 6H). 13C NMR (101 MHz, CDCl3) d155.1, 143.2, 137.0, 130.3, 122.2, 107.0, 56.6. HRMS (EI): Exactmass calculated for C14H12N2O2: 240.0899, found 240.0894(1.8 ppm). 1H- and 13C NMR data are in accordance with published literature.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-3-methoxyaniline, and friends who are interested can also refer to it.

Reference:
Article; Viktorsson, Elvar Oern; Melling Gr°the, Bendik; Aesoy, Reidun; Sabir, Misbah; Snellingen, Simen; Prandina, Anthony; H°gmoen ?strand, Ove Alexander; Bonge-Hansen, Tore; D°skeland, Stein Ove; Herfindal, Lars; Rongved, Pal; Bioorganic and Medicinal Chemistry; vol. 25; 7; (2017); p. 2285 – 2293;,
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Application of 22236-10-8, 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. 22236-10-8 name is 4-(Difluoromethoxy)aniline, 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.

Example 12; 2-ButyI-5-(4-chIorophenyl)-4-{[4-(difluoromethoxy)phenyl]amino}isothiazol-3(2H)-one 1,1-dioxide; 2-Butyl-4-chloro-5-(4-chlorophenyl)isothiazol-3(2H)-one 1,1-dioxide (0.2Og, 0.60mmol) and 4-(difiuoromethoxy)-aniline (0.19Og, 1.20mmol) were mixed in MeCN (2.5mL). The mixture was heated in a microwave reactor at 130 C for 15 mins, then additional 60 mins and then at 140 0C for 15 mins, then additional 30 mins. The mixture was evaporated and the residue was purified by column chromatography (ISOLUTE SI 20 g/70 mL), eluting with heptane, then DCM:heptane (25:75, then 50:50), to give the title compound (0.122g, 45%);

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

Reference:
Patent; ASTRAZENECA AB; WO2006/73363; (2006); A1;,
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Adding a certain compound to certain chemical reactions, such as: 22171-15-9, name is (4-(Benzyloxy)phenyl)methanamine, belongs to ethers-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 22171-15-9, Recommanded Product: 22171-15-9

2,6-Diamino-nicotinic acid described in Preparation Example A-15 (0.6g, 3.92mmol), triethylamine (1.64mL, 11.8mmol) and benzotriazole-1-yloxy tris(dimethylamino)phosphonium hexafluorophosphate (2.6g, 5.9mmol) were dissolved in N,N-dimethylformamide (200mL), 4-benzyloxy-benzylamine described in Preparation Example 1 (1.25g, 5.9mmol) was added thereto, and the solution was stirred at room temperature for 16 hours. After the reaction was completed, the reaction solution was poured into brine, and the solution was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, then concentrated, the obtained residue was purified by NH silica gel column chromatography (ethyl acetate : hexane = 2 : 1, then ethyl acetate), the resulting solid was washed with solvent (chloroform : ethyl acetate = 2 : 1), and the title compound (0.37g, 1.1 mmol, 27%) was obtained. 1H-NMR Spectrum (DMSO-d6) delta(ppm) : 4.29 (2H, d, J=6.0Hz), 5.07 (2H, s), 5.66 (1H, d, J=8.4Hz), 6.06 (2H, br s), 6.91-6.97 (4H, m), 7.19 (2H, d, J=8.8Hz), 7.29-7.45 (5H, m), 7.65 (1H, d, J=8.4Hz), 8.27 (1H, t, J=6.0Hz).

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, (4-(Benzyloxy)phenyl)methanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Eisai Co., Ltd.; EP1669348; (2006); A1;,
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Adding a certain compound to certain chemical reactions, such as: 102503-23-1, name is 1-(2,4-Dimethoxyphenyl)-N-methylmethanamine, belongs to ethers-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 102503-23-1, HPLC of Formula: C10H15NO2

Sodium hydride (60% in oil, 2.23 g, 55.8 mmol) was washed twice with n-hexane and suspended in THF (180 mL). A solution of 1-(2,4-dimethoxyphenyl)-N-methylmethanamine (9.09 g, 50.2 mmol) in THF (10 mL) was added dropwise to this suspension at 0 C, and then the mixture was stirred at 60 C for 18 h. After cooled to 0 C, a solution of compound 15 (9.64 g, 45.4 mmol) in THF (10 mL) was added dropwise, and then the mixture was stirred at the same temperature for 1 h. Ice-cooled solution of NaCl were added, and the mixture was extracted with EtOAc. The extract was washed successively with a solution of NH4Cl, a solution of NaHCO3, H2O and brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (EtOAc) to obtain compound 16 (16.8 g, 99%) as a yellow oil. 1H-NMR (CDCl3) d 2.24 (3H, s), 3.51 (2H, s), 3.54 (2H, s), 3.79 (3H, s), 3.80 (3H, s), 6.45 (1H, s), 6.42-6.50 (1H, m), 6.68 (1H, dd, J = 4.7 Hz, 3.6 Hz), 7.18-7.29 (2H, m), 7.98 (1H, ddd, J = 4.5 Hz, 1.9 Hz, 1.5 Hz), 8.25 (1H, ddd, J = 10.2 Hz, 8.0 Hz, 1.9 Hz), 8.67 (1H, s).

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:
Article; Nishida, Haruyuki; Fujimori, Ikuo; Arikawa, Yasuyoshi; Hirase, Keizo; Ono, Koji; Nakai, Kazuo; Inatomi, Nobuhiro; Hori, Yasunobu; Matsukawa, Jun; Fujioka, Yasushi; Imanishi, Akio; Fukui, Hideo; Itoh, Fumio; Bioorganic and Medicinal Chemistry; vol. 25; 13; (2017); p. 3447 – 3460;,
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Related Products of 6851-80-5, 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. 6851-80-5, name is 1-(2-Methoxyphenyl)-N-methylmethanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: The mixture of secondary amine (1.01 mmol) and paraformaldehyde(1.01 mmol) in ethanol (3 mL) was refluxed for 1 h,until paraformaldehyde was dissolved. Then compound 5 or 6(100 mg, 0.34 mmol) was added in one portion. The reactionmixture was refluxed for 24e48 h. Ethanol was removed underreduced pressure. The residue was diluted with water and acidifiedwith an aqueous solution of hydrochloric acid (10%). The aqueousphase was washed with CH2Cl2, and then basified with saturatedNaHCO3 solution. The alkaline aqueous phase was again extractedwith CH2Cl2. The combined organic phase washed with brine, driedover Na2SO4, filtered and concentrated under reduced pressure toafford the corresponding crude aurone Mannich base derivatives.Additionally, compounds 8a-b and the corresponding 9a-b wereobtained in one pot.

The synthetic route of 1-(2-Methoxyphenyl)-N-methylmethanamine has been constantly updated, and we look forward to future research findings.

Reference:
Article; Li, Yan; Qiang, Xiaoming; Luo, Li; Yang, Xia; Xiao, Ganyuan; Liu, Qi; Ai, Jiachen; Tan, Zhenghuai; Deng, Yong; European Journal of Medicinal Chemistry; vol. 126; (2017); p. 762 – 775;,
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3616-56-6, name is 2,2-Diethoxy-N,N-dimethylethanamine, belongs to ethers-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. category: ethers-buliding-blocks

Synthesis Example B6Synthesis of 12H-benzofuranyl[3,2-a]carbazole (compound 6)Compound 5 (2.8 g, 1 eq.) is added to acetic acid (30 ml) and heated to reflux. (Dimethylamino)acetaldehyde diethyl acetal (95percent; 20.3 g, 10 eq.) is added dropwise in portions to the solution.The reaction is stirred at reflux overnight.Then further (dimethylamino)acetaldehyde diethyl acetal (95percent; 2.0 g) is added and stirred further at reflux after 3 h.Subsequently, the flask contents are diluted with CH2Cl2 at room temperature and washed in a separating funnel with distilled water and NaCl (saturated).Organic phase is dried with Na2SO4 and concentrated. LC (SiO2, 15:85 ethyl acetate/cyclohexane) gives the product 6 (1.92 g, 62.2percent yield).1H NMR (CD2Cl2, 400 MHz): delta=8.88 (br s, 1H), 8.16 (d, 1H), 8.12 (d, 2H), 7.66 (d, 1H), 7.62 (d, 1H), 7.42-7.53 (m, 4H), 7.31 (dd, 1H).

The synthetic route of 3616-56-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BASF SE; OSRAM OPTO SEMICONDUCTORS GMBH; KONINKLIJKE PHILIPS ELECTRONICS N.V.; US2011/266528; (2011); A1;,
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Reference of 54149-17-6, These common heterocyclic compound, 54149-17-6, name is 1-Bromo-2-(2-methoxyethoxy)ethane, 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.

2,7-dibromofluorene (Sigma Aldrich) (15.7 g, 0.048 mol) was dissolved in anhydrous tetrahydrofuran (150 mL) and cooled to 5 C. under argon atmosphere. Sodium tert-butoxide (10.5 g, 0.109 mol) was added portionwise, giving a deep red colour. After completion of addition, the reaction mixture was stirred at room temperature for 20 minutes. A solution of 1-bromo-2-(2-methoxyethoxy)ethane (Sigma Aldrich) (20 g, 0.109 mol) in anhydrous THF (50 mL) was added dropwise. The solution turned dark purple and an exotherm to 30 C. was observed. The reaction mixture was stirred at room temperature for 72 hours then diluted with water and ethyl acetate. The layers were separated and the aqueous phase extracted with ethyl acetate (2*). The combined organic layers were washed with water and brine then dried (Na2SO4) and filtered. Concentration of the filtrates in vacuo followed by purification of the residue by dry flash chromatography (0 to 40% ethyl acetate in heptane) gave 2,7-dibromo-9,9-Bis[2-(2-methoxyethoxy)ethyl]-9H-fluorene as a yellow oil (10 g, 40%). 1H NMR (300 MHz, CDCl3) 7.52-7.42 (m, 6H), 3.27 (m, 10H), 3.16 (m, 4H), 2.76 (m, 4H), 2.34 (m, 4H).

Statistics shows that 1-Bromo-2-(2-methoxyethoxy)ethane is playing an increasingly important role. we look forward to future research findings about 54149-17-6.

Reference:
Patent; Wuhan Xinqu Chuangrou Optoelectronics Technology Co., Ltd.; SIMMS, Michael James; OGIER, Simon Dominic; (47 pag.)US2019/131533; (2019); A1;,
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