Category: ethers-buliding-blocks

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. 106854-77-7, name is 1-Bromo-4-(2,2,2-trifluoroethoxy)benzene, A new synthetic method of this compound is introduced below., category: ethers-buliding-blocks

1-BROMO-4- (2, 2,2-trifluoroethoxy) benzene (1) (0.85 g, MW 255.03, 1.5 eq), pinacol diborane (from Aldrich, 0.89 g, MW 253.95, 1.6 eq), potassium acetate (from Aldrich, 0.86 g, MW 98.15, 4.0 eq), and (1, 1′-BIS (diphenylphosphino)- ferrocene) dichloropalladium (II) complex with dichloromethane (from Aldrich, 54 mg, MW 816.64, 0.03 eq) were charged in a round-bottom flask. The flask was purged with N2. N, N-DIMETHYLFORMAMIDE (from Aldrich, 8.0 ml) was then added, and the mixture was stirred at 80C for 2 hr. Tert-butyl 4-[(6-BROMOPYRIDIN-3-YL) SULFONYL] tetrahydro-2H-pyran- 4-carboxylate (2) (0.90 g, MW 406.29) was then added, along with sodium carbonate solution (2 M aqueous, 5.5 ml, 5 eq) and additional palladium complex (above, 54 mg, 0.03 eq). The reaction was continued at 80C for 3 hr. Afterward, the mixture was cooled to room temperature and filtered through a Celite pad. The filter cake was washed with ethyl acetate (2 x 50 ml). The filtrate and washes were then combined and washed with water (3 x 100 ml) and brine (1 x 100ML). The organics were then dried over sodium sulfate and concentrated to form a black residue. The residue was chromatographed (silica gel, ethyl acetate: hexanes, 1: 5) to afford TERT-BUTYL-4- (F 6- [4- (2, 2,2- TRIFLUOROETHOXY) phenyl] pyridin-3-yl} sulfonyl) tetrahydro-2H-pyran-4-carboxylate (3) as a white solid (0.26 g, 24 % yield). The product (3) was confirmed by LCMS. The “equivalents”above indicate equivalents relative to the charged amount OF TERT-BUTYL 4- [ (6- bromopyridin-3-yl) sulfonyl] TETRAHYDRO-2H-PYRAN-4-CARBOXYLATE.

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; PHARMACIA CORPORATION; WO2004/48368; (2004); A2;,
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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. 2674-34-2, name is 1,4-Dibromo-2,5-dimethoxybenzene, A new synthetic method of this compound is introduced below., Recommanded Product: 1,4-Dibromo-2,5-dimethoxybenzene

The 1,4-dibromo-2,5-dimethoxybenzene (T-13) (25.0g, 84.47mmol, Tokyo Kasei Kogyo),4-methoxyphenyl boronic acid (T-14) (28.2g, 185.84mmol, Tokyo Kasei Kogyo),Bis (di – t-butyl (4-dimethylaminophenyl) phosphine) dichloropalladium (II)(0.30g, 0.42mmol),Trisodium phosphate dodecahydrate (96.33g, 253.42mmol),Tetrabutylammonium bromide (TBAB) (5.45g, 16.89mmol),Toluene (100ml), isopropanol (100ml)And water(100ml) were mixedIt was heated at reflux for 5 hours.The reaction mixture was allowed to cool to room temperature filtered,The filtrate was washed with water (200ml) and saturated brine (100ml) washedDried over anhydrous magnesium sulfate,Concentrated under reduced pressure.By column chromatography (the eluent:Toluene / ethyl acetate = 9/1 (volume ratio)) and the residue was purified,To obtain the compound (T-15) (27.9g, 84.47mmol, 94.3%).

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; JNC Co., Ltd.; JNC Petrochemical Co., Ltd.; Kobayashi, Masahide; Goto, Yasuyuki; Kobayashi, Takahiro; (94 pag.)CN105358523; (2016); A;,
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These common heterocyclic compound, 6876-00-2, name is 1-Bromo-3-phenoxybenzene, 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. COA of Formula: C12H9BrO

EXAMPLE 31 1-(2,4-Difluorophenyl)-1-(2-fluoro-3-(3-phenoxyphenyl)prop-1-enyl)cyclopropane The method of Example 25 was repeated using a Grignard reagent, prepared from 3-phenoxyphenyl bromide (0.28 g), tetrahydrofuran (2 ml), magnesium (22 mg) and 1-(3-acetoxy-2-fluoroprop-1-enyl)-1-(2,4-difluorophenyl)cyclopropane (Example 23) (0.1 g). The residue after evaporation was purified by preparative thin layer chromatography (solvent: diethyl ether/hexane; 1:9) and then preparative high performance liquid chromatography (column: C8; solvent: methanol; flow rate: 2 ml/min) to afford 1-(2,4-difluorophenyl)-1-(2-fluoro-3-(3-phenoxyphenyl)prop-1-enyl)cyclopropane (80 mg, 56%).

The synthetic route of 1-Bromo-3-phenoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; British Technology Group Limited; US5763700; (1998); A;,
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Some common heterocyclic compound, 216067-66-2, name is O-(2,4-Dimethoxybenzyl)hydroxylamine, molecular formula is C9H13NO3, 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. Formula: C9H13NO3

6-Amino-hexanoic acid (13.1 g, 100 mmoL) was dissolved in 10% aqueous Na2CO3 solution (300 mL), then dioxane (200 mL) was added to the above solution. Fmoc-CI (26 g, 110 mmoL) was added to the above mixture portion-wise, and the resultant reaction mixture was stirring for 12h. The mixture was extracted with ether (150 mL X 2), and the aqueous portion was acidified by 6N HCI. The mixture was filtered, and the solid was washed with water and dried to give 6- (9H-Fluoren-9-ylmethoxycarbonylamino)-hexanoic acid as a white solid (31 g, 81 %). 6- (9H-Fluoren-9-ylmethoxycarbonylamino)-hexanoic acid (9.17 g, 25 mmoL) and 0- (2, 4- dimethoxy-benzyl)-hydroxylamine (36 g, 26 mmoL) were dissolved in DCM (250 mL), then DCC (6.18 g, 30 mmoL) was added ortion-wise. The resultant mixture was stirred for 3h at room temperature, then cooled to 0C, filtered, and washed with DCM. The organic solution was evaporated to dryness to give the crude [5- (2, 4-dimethoxy- benzyloxycarbamoyl)-pentyl]-carbamic acid 9H-fluoren-9-ylmethyl ester. The crude ester was reacted with piperidine (5 mL) in MeOH (150 mL) at room temperature for12 h. The solution was evaporated and the residue was purified by flash chromatography (silica, EtOAc: MeOH = 5: 1). 6-Amino-hexanoic acid (2,4-dimethoxy- benzyloxy)-amide was obtained as a white solid (4.15 g, 56%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 216067-66-2, its application will become more common.

Reference:
Patent; S*BIO PTE LTD; WO2005/40101; (2005); A1;,
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Some common heterocyclic compound, 24988-36-1, name is 1,5-Dibromo-2,4-dimethoxybenzene, molecular formula is C8H8Br2O2, 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. Recommanded Product: 24988-36-1

Bisdimethylaminoethyl ether (2.84 g) was dissolved in 42 mL THF and cooled in an ice bath. Isopropylmagnesium chloride (8.9 mL of a 2 M solution in THF) followed by Compound 14 (5 g dissolved in 5 mL THF) were added slowly sequentially. The mixture was allowed to warm to ambient temperature and stirred overnight. Next, 2.1 mL of 3-chloro-2-fluorobenzaldehyde was added. After stirring for ~ Ih, the mixture was quenched to pH ~ 7 with 2N HCl. The product was extracted into ethyl acetate and the organic phase was dried over sodium sulfate. The solvent was exchange to heptane to precipitate the product and a mixture of heptanes:MTBE (4:1) was added to form a slurry. After filtration the solid was slurried in toluene, filtered and vacuum dried to yield compound 15: 1U NMR (CD3CN, 400 MHz) delta 7.47 (s, IH), 7.41-7.35 (m, 2H), 7.15 (t, J = 7.4 Hz, IH), 6.66 (s, IH), 6.21 (br s, IH), 3.90 (s, 3H), 3.87 (br s, IH), 3.81 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 24988-36-1, its application will become more common.

Reference:
Patent; GILEAD SCIENCES, INC.; WO2009/36161; (2009); A1;,
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Electric Literature of 29026-74-2, The chemical industry reduces the impact on the environment during synthesis 29026-74-2, name is 2-Isopropoxyaniline, I believe this compound will play a more active role in future production and life.

EXAMPLE 4 Ethyl 1,6-dihydro-2-methylthio-6-oxo-5-pyrimidinecarboxylate (15 g) and 2-(1-methylethoxy)aniline (11.5 g) are added to ethanol (100 ml), and the mixture is refluxed with stirring for 17 hours. After cooling, the precipitate is collected by filtration and recrystallized from DMF to give ethyl 1,6-dihydro-2-[2-(1-methylethoxy)anilino]-6-oxo-5-pyrimidinecarboxylate (8.5 g). M.p. 205-207 C. Elemental analysis for C16 H19 N3 O4: Calcd. (%): C, 60.56; H, 6.03; N, 13.24. Found (%): C, 60.73; H, 6.12; N, 13.40. IR numaxnujol cm-1: 3000-3300 (NH), 1720 (C=O), 1600 (C=O). NMR (DMSO-d6) delta: 1.34 (6H, d, J=7 Hz, OCH(CH3)2), 1.30 (3H, t, J=7 Hz, OCH2 CH3), 4.26 (2H, q, J=7 Hz, OCH2 CH3), 4.73 (1H, m, OCH(CH3)2), 6.86-7.30 (3H, m, Ar–H), 8.32 (1H, d, J-8 Hz, Ar–H), 8.53 (1H, s, C4 –H), 8.20-12.30 (2H, b, 2*NH). Mass m/e: 317 (M+).

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-Isopropoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Morishita Pharmaceutical Co. Ltd.; US4666915; (1987); A;,
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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. 24332-20-5, name is 1,1,2-Trimethoxyethane, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1,1,2-Trimethoxyethane

A solution of 1,1,2-trimethoxyethane (838 mg, 6.9 mmol, 901.3 uL) in water (22.0 mL) and HC1 (0.3 mL, 2M) was stirred at 60C for 2h, then extracted with dichloromethane (10.0 mL x 3). The combined organic layers were washed with brine (30.0 mL x 3), dried over Na2 SO4, filtered to give a filtrate. To the filtrate was added the solution of 2-((lr,4r)-4- aminocyclohexyl)isoindoline-1,3-dione (500 mg, 1.4 mmol, TFA) with TEA to pH 7 in MeOH (30.0 mL) and CH3COOH (125 mg, 2.0 mmol, 119.7 uL). And then NaBH3CN (175 mg, 2.7 mmol) was added to above reaction mixture and CH3COOH was added to adjusted pH to 5. The mixture was stirred at 60C for 12 h. The reaction mixture was extracted with dichloromethane (30.0 mL x 3). The combined organic layers were washed with brine (30 mL x 3), dried over Na2SO4, filtered and concentrated under reduced pressure to give 2-((lr,4r)-4-((2- methoxyethyl)amino)cyclohexyl)i soindoline- 1,3 -dione (410 mg, crude).

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 24332-20-5.

Reference:
Patent; QUENTIS THERAPEUTICS, INC.; VACCA, Joseph P.; LI, Dansu; BETTIGOLE, Sarah; (143 pag.)WO2018/222917; (2018); 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. 702-24-9, name is 4-Methoxy-N-methylbenzylamine, A new synthetic method of this compound is introduced below., SDS of cas: 702-24-9

General procedure: A solution of 2-methyl-4-chlorocyclopenta[d]pyrimidine (17, 1eq.) and appropriate anilines or benzylamines (1.05 eq.) wereplaced in dioxane in a microwave vial. To the solution, HCl (2Nin dioxane, 1?2 drops) was added. The reaction mixture was setin a Biotage microwave initiator at 120 C for 3?6 h with pressure<4 bar. The reaction was cooled and transferred to a flask, and thesolvent was evaporated at reduced pressure. The residue wasdiluted with EtOAc, neutralized with NH4OH, and then washedwith water (2 10 mL). After drying with anhydrous Na2SO4, theorganic solvent was concentrated in a rotary evaporator to <1mL. This residue was placed on top of a silica gel column and elutedwith hexane and EtOAc or with CHCl3 and MeOH. Fractions containingthe product (TLC) were pooled and evaporated to affordpure compounds 3?7, 9?14. 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:
Article; Xiang, Weiguo; Choudhary, Shruti; Hamel, Ernest; Mooberry, Susan L.; Gangjee, Aleem; Bioorganic and Medicinal Chemistry; vol. 26; 9; (2018); p. 2437 – 2451;,
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Adding a certain compound to certain chemical reactions, such as: 111-95-5, name is Bis(2-methoxyethyl)amine, 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 111-95-5, SDS of cas: 111-95-5

Example 2 8.0 g (60 mmol) of bis(methoxyethyl) amine was added to 100 ml of dehydrated dichlorrmethane in a flask followed by Ar gas replacement. Thereafter, 8.8 g (87 mmol) of triethyl amine was added thereto. Next, the system was cooled down to about -10 C. 6.5 g (72 mmol) of acrylic acid chloride was slowly dropped in the system while keeping the temperature in the system ranged from -10 C. to -5 C. and thereafter stirred for two hours at room temperature. Furthermore, subsequent to removal of precipitants by filtration, the filtrate was washed with saturated sodium hydrogen carbonate aqueous solution and saturated sodium chloride aqueous solution. Next, subsequent to drying by sodium sulfate, the dried resultant was condensed under a reduced pressure to obtain an oily brown material. (0184) Furthermore, by a column chromatography filled with 300 g of Wakogel C300 (manufactured by Wako Pure Chemical Industries, Ltd.) using hexane and ethyl acetate as eluate, the oily brown material was fined to obtain 5.5 g (yield: about 50%) of an oily, pale yellow material represented by the following chemical formula. 1H-NMR (CDCl3): delta3.34 (d, 6H), 3.51 (t, 2H), 3.57 (t, 2H), 3.63 (t, 4H), 5.67 (dd, 1H), 6.34 (dd, 1H), 6.64-6.69 (m, 1H) IR(NaCl): 2982, 2930, 2981, 2829, 1651, 1613, 1447, 1366, 1315, 1270, 1230, 1193, 1157, 1118, 1069, 1015, 981, 962, 824, 795, 529 cm-1

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Bis(2-methoxyethyl)amine, and friends who are interested can also refer to it.

Reference:
Patent; Ricoh Company, Ltd.; Morita, Mitsunobu; Noguchi, Soh; Kimura, Okitoshi; (28 pag.)US9593248; (2017); B2;,
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Electric Literature of 29578-39-0, These common heterocyclic compound, 29578-39-0, name is 1-Bromo-3-fluoro-5-methoxybenzene, 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.

Step 2 3-Bromo-5-fluorophenol To a solution of 1-bromo-3-fluoro-5-methoxybenzene (3.0 g, 0.015 mol) in dry CH2Cl2 (80 mL) under an inert atmosphere and cooled to -30 C. was added 1 M BBr3 (4.27 mL, 0.045 mol) in 21 mL of CH2Cl2 dropwise while maintaining temperature at -30 C. The reaction was stirred for 3 h at 0-5 C. and then the reaction mixture was quenched with aqueous saturated NaHCO3. Water was added and the mixture was extracted with CH2CO2 three times. The organic layer was washed with brine, dried over Na2SO4 and evaporated to dryness to give the title compound (2.54 g, 91%).

The synthetic route of 29578-39-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FAY, Lorraine Kathleen; Johnson, Douglas S.; Kesten, Suzanne Ross; Lazerwith, Scott E.; Morris, Mark Anthony; Stiff, Cory Michael; Meyers, Marvin Jay; Wang, Lijuan Jane; US2008/261941; (2008); A1;,
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