Tag: M.W=200-300

Synthetic Route of 3469-00-9,Some common heterocyclic compound, 3469-00-9, name is Methyl Diphenylacetate, molecular formula is C15H14O2, 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 diisopropylamine (0.17 mL, 1.19 mmol) in THF (1 mL) was added n-BuLi (2.5 M in hexane, 0.4 mL, 0.994 mmol) at -78 C. The reaction mixture was stirred at this temperature for 30 min, followed by stirring at -5 C for 30 min. Then, the reaction mixture was cooled to -78 C and diphenyl methylacetate (S6) (0.15 g, 0.66 mmol) in THF (2 mL) was added. After stirring at -78 C for 15 min, (E)-4,6-iodoheptadiene (S11) (0.16 g, 0.72 mmol) was added. The resulting solution was stirred at rt overnight. The reaction mixture was quenched with satd aq NH4Cl (10 mL) and extracted with EtOAc (2 x 50 mL). The extract was washed with water and brine, dried (MgSO4), filtered, and concentrated by rotary evaporation. Column chromatography of the residue (20:1 hexane/EtOAc) gave S12 (120 mg, 63%) as colorless oil.

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

Reference:
Article; Chandrasekhar; Ryu, Jae-Sang; Tetrahedron; vol. 68; 24; (2012); p. 4805 – 4812;,
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Related Products of 653-92-9, 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 653-92-9 as follows.

(b) Methyl 2-cyano-4-fluorobenzoate; Methyl 2-bromo-4-fluorobenzoate (1.0 g, 4.29 mmol; see step (a) above) was dissolved in dry DMF (5 mL) and degassed with N2-gas for 5 minutes. CuCN (769 mg, 8.58 mmol) was added and mixture was degassed again before the temperature was raised. The reaction mixture was refluxed for 75 minutes. NaCN (aq, 10%) was added and the mixture was extracted with DCM. The DCM phase was dried through a phase separator and the solvent was removed in vacuo. The crude product was dissolved in toluene and washed once with water. The organic phase was dried over MgS04 and filtered. The solvent was removed in vacuo to give the product (in 94% yield), which was used without further purification. ‘H NMR (500 MHz, CDC13) 5 4.01 (s, 3H), 7.35-7. 42 (m, 1H), 7.52 (dd, 1H), 8.15-8. 23 (m, 1H)

According to the analysis of related databases, 653-92-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; WO2005/58826; (2005); A1;,
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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. 185312-82-7, name is Methyl 4-bromo-2-chlorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C8H6BrClO2

To a stirred solution of 4-bromo-2-chlorobenzoic acid, methyl ester (18.69 g) in triethylamine (110 ml), was added 1-dimethylamino-2-propyne (12.1 ml), bis(triphenylphosphine)palladium(II) chloride (1.26 g), and copper(I) iodide (0.136 g). The mixture was heated slowly to 60 C., and the temperature maintained for one hour. The reaction was cooled to room temperature, filtered through diatomaceous earth, and the collected solid washed with ethyl acetate. The solvent was removed in vacuo, the resulting residue redissolved in ethyl acetate, and washed with water (3¡Á). The combined organic extract was dried over anhydrous sodium sulfate, and the solvent removed in vacuo to give a crude product. The crude product was purified by column chromatography on silica gel (225 g), eluting with 40% ethyl acetate/hexane. After removing the solvent in vacuo, the title compound was obtained as a viscous oil (17.7 g), MS (+FAB), m/z: 252 (M+H)+.

The synthetic route of 185312-82-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; American Cyanamid Company; US6831079; (2004); B1;,
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Reference of 17100-65-1, 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 17100-65-1 as follows.

[0162] Step c: To a reaction vial containing 7-amino-4-chloro-isoindolin-l-one (250 mg, 1.37 mmol) in dioxane (10 mL) was added methyl 2-bromo-5-methoxy-benzoate (502 mg, 2.05 mmol), cesium carbonate (893 mg, 2.74 mmol), copper iodide (104 mg, 0.55 mmol) and (1S,2S)- Nl,N2-dimethylcyclohexane-l,2-diamine (156 mg, 1.1 mmol). The mixture was purged with nitrogen, then warmed to 110 C. The reaction was stirred at 110 C for lh and the reaction was monitored by LC-MS. Following completion, the reaction was allowed to cool and was then filtered through Celite and rinsed with ethyl acetate. The crude was purified by silica gel chromatography (0-50% ethyl acetate/hexane) to give methyl 2-(7-amino-4-chloro-l-oxo- isoindolin-2-yl)-5-methoxy-benzoate. MS: (ES) m/z calculated for CI7HI5C1N204[M+H]+347.1, found 347.1.

According to the analysis of related databases, 17100-65-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHEMOCENTRYX, INC.; CHEN, Xi; DRAGOLI, Dean, R.; FAN, Junfa; KALISIAK, Jaroslaw; LELETI, Manmohan, Reddy; MALATHONG, Viengkham; MCMAHON, Jeffrey; TANKAKA, Hiroko; YANG, Ju; YU, Chao; ZHANG, Penglie; MALI, Venkat; (104 pag.)WO2017/87610; (2017); A1;,
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Application of 105-76-0, These common heterocyclic compound, 105-76-0, name is Dibutyl maleate, 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 6 Dibutyl N-Hydroxyaspartate Hydroxylamine free base (50% aqueous solution, 8.0 g, 0.12 mol) was added dropwise to dibutyl maleate (25.0 g, 0.1 mol) in a 3-neck 250 ml flask blanketed with nitrogen. The reaction temperature was maintained below 55 C. with an ice bath. The mixture was stirred for 30 minutes. The gas liquid chromatography (GLC) analysis of the reaction mixture indicated 96% conversion of dibutyl maleate. The NMR analysis showed that the reaction mixture contained dibutyl N-hydroxyaspartate in greater than 95% purity.

The synthetic route of 105-76-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hoechst Celanese Corporation; US5322948; (1994); A;,
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Reference of 59247-47-1, These common heterocyclic compound, 59247-47-1, name is tert-Butyl 4-bromobenzoate, 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.

INTERMEDIATE 1(R>4-[2-(4-CHLOROPHENYL)-l-PROPYLETHAN-2-ONE-l-YL]BENZOIC ACID TERT-BUTYL ESTER15 Step A. tert-Butyl 4-[2-f4-Chlorophenyl)-l-propylethan-2-one-l-yllbenzoateA 3-neck flask was charged with NaOtBu (2.85 g, 28.6 mmol) and dry THF (50 mL) under nitrogen. Tris(dibenzylideneacetone)dirhoaIladium(0) (0.26 g, 0.28 mmol) and (S)-ToI- Binap (0.47 g, 0.69 mmol) were then added under nitrogen. After stirring for 15 min, l-(4-20 chlororhohenyl)rhoentan-l-one (4.21 g, 21.0 mmol) was added, followed by tert-butyl 4- bromobenzoate (5.0 g, 19.1 mmol) under nitrogen. The mixture was heated at 6O0C for 8 hours. The mixture was diluted with heptane (100 mL) and poured into a solution of saturated NaHCO3 (aq) (60 mL) and ice (40 g). The resulting layers were separated, and the aqueous phase was back-extracted with methyl tert-butyl ether (50 mL). The combined organics were washed with25 saturated NaHCO3 (aq) then 10percent NaCl (aq). The organic solution was filtered through a bed of MRL DOB-0000Ssilica 60 (84 g, wetted with 1 : 1 methyl tert-butyl ether/heptane), and washed with 1 : 1 methyl tert-butyl ether/heptane (600 mL). The combined filtrate was concentrated to afford an orange oil that was used directly for the next step: 1H NMR (500 MHz, CDCl3): delta 7.91 (d, J – 8.1 Hz5 2 H); 7.86 (d, J = 8.4 Hz, 2 H); 7.35 (d, J = 8.4 Hz5 2 H); 7.32 (d, J = 8.2 Hz, 2 H); 4.53 (t, J = 5 7.2 Hz5 1 H); 2.19-2.09 (m, 1 H); 1.85-1.76 (m. 1 H); 1.56 (s, 9 H); 1.35-1.18 (m, 2 H); 0.91 (t, J = 7.3 Hz, 3 H); LCl: 1.35 min. (M-tBu+H) = 317.

The synthetic route of 59247-47-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIN, Songnian; STEVENSON, Christian, P.; PARMEE, Emma, R.; XU, Libo; LIAO, Xibin; METZGER, Edward; LIANG, Rui; ZHANG, Fengqi; STELMACH, John, E.; WO2010/30722; (2010); A1;,
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Synthetic Route of 685892-23-3, 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 685892-23-3 as follows.

Step 1. Preparation of methyl 2-chloro-6-cyclobutylbenzoate (i-llb).A mixture of methyl 2-bromo-6-chlorobenzoate (i-ha) (750 mg, 3 mmol), (PPh3)4Pd (345 mg, 0.3 mmol) and cyclobutylzinc bromide (12 ml in THF, 6 mmol) were mixed under N2 protection. The mixture was stirred at 70C for 12 h under N2. The mixture was extracted with EtOAc and water. The organic phase was washed with brine, dried over Na2SO4, filtered, concentrated, and purified with chromatography (PE: EtOAc = 50:1) to give 350 mg (61% inLCMS, contained some PPh3) of the title compound. LCMS (ESI) calc?d for C12H13C102 [M+H]: 225, found: 225.

According to the analysis of related databases, 685892-23-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BARR, Kenneth Jay; MACLEAN, John; ZHANG, Hongjun; BERESIS, Richard Thomas; WO2014/28600; (2014); A2;,
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Electric Literature of 150529-73-0, A common heterocyclic compound, 150529-73-0, name is Methyl 2-(3-bromophenyl)acetate, molecular formula is C9H9BrO2, 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 1-To a solution of 216a (1.19 g, 5 mmol) in CCl4 (30 mL) was added NBS (1.08 g, 6 mmol) followed by benzoyl peroxide (catalytic quantity). The mixture was heated at 80 C. overnight. Then the mixture was cooled, filtered and the solid washed with hexane. The combined filtrates were concentrated in vacuo to afford 1.58 g (100%) of 216b as yellow oil.

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; Roche Palo Alto LLC; US2008/146595; (2008); A1;,
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Application of 107317-58-8, 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 107317-58-8 as follows.

To a solution of methyl 4-bromo-3-(trifluoromethyl)benzoate (10 g, 35.33 mmol) in THF (100 mL) under nitrogen was added 2 M lithium borohydride in THF (2.309 g, 106.0 mmol). The mixture was heated at reflux. The mixture was cooled to 0C and carefully quenched with 6 N HC1 (aq) (about 20 mL or less) (vigorous in the beginning 3-5 mL) up to pH 3. The mixture was diluted with water (25 mL) and extracted with EtOAc (2X). The combined organics were dried over anhydrous Na2S04and filtered. The filtrate was concentrated in vacuo to dryness to afford the crude (4-bromo-3- (trifluoromethyl)phenyl)methanol as a brown solid.

According to the analysis of related databases, 107317-58-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; SADEQUE, Abu J.M.; BUZARD, Daniel J.; (82 pag.)WO2020/51378; (2020); A1;,
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Application of 91-44-1, A common heterocyclic compound, 91-44-1, name is 7-(Diethylamino)-4-methyl-2H-chromen-2-one, molecular formula is C14H17NO2, 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 25 mL reaction tube, add Na2CO3 (63.6 mg, 0.60 mmol), 69.4 mg (0.30 mmol, 1 equivalent) of compound C-2,After replacing with argon three times, 1 mL of acetone (Acetone) + 1 mL of N, N-methylformamide (DMF) was added.After injecting 132 muL (0.90 mmol) of compound E-1 and stirring under blue light for 24 hours, compound H-2 was obtained with a yield of 95%.

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; Zunyi Medical University; He Chunyang; Mao Ting; Zhao Liang; Li Xiaofei; (13 pag.)CN110642831; (2020); A;,
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