Tag: M.W=200-300

Some common heterocyclic compound, 82702-31-6, name is Methyl 3-bromo-4-fluorobenzoate, molecular formula is C8H6BrFO2, 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. HPLC of Formula: C8H6BrFO2

To methyl 3-bromo-4-fluorobenzoate (3.02 g, 13.0 mmol) in ether (30 ml) at 0 C. add dropwise MeMgBr (3.0M in ether, 11 ml, 33 mmol). Stir 1 h and pour onto ice. Acidify with 1N HCl, separate the ether, wash with 1N NaHCO3, dry (MgSO4), and concentrate to obtain the product as a 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 82702-31-6, its application will become more common.

Reference:
Patent; Schering Corporation; US2005/239795; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

105-76-0, name is Dibutyl maleate, belongs to esters-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. Quality Control of Dibutyl maleate

Example 3 N-(3-Triethoxysilylpropyl)-aspartic acid di-n-butyl ester 221.0 g (1.0 mol) of 3-aminopropyl-triethoxysilane and 228.0 g (1.0 mol) of maleic acid di-n-butyl ester were reacted by the same procedure used in Example 1. The viscosity of the clear, pale yellow liquid was about 30 mPa.s (23 C). Base titration showed an amine equivalent weight of about 462 g (theory: 449 g).

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

Reference:
Patent; Bayer Aktiengesellschaft; US5364955; (1994); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 619-42-1,Some common heterocyclic compound, 619-42-1, name is Methyl 4-bromobenzoate, molecular formula is C8H7BrO2, 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 stirred solution at room temperature of methyl 4-bromobenzoate (8.84 g, 41.11 [MMOL),] Pd [(PPH3)] 2Cl2 (840 mg, 1.20 [MMOL)] and Cul (455 mg, 2.39 [MMOL)] in anhydrous THF (200 ml) was saturated with nitrogen for 15 min. Then, the solution under nitrogen was cooled down at [0C,] and [TRIMETHYLSILYLACETYLENE] (7.2 [ML,] 50.91 [MMOL)] and triethylamine (22 [ML,] 157.8 [MMOL)] were added successively. The reaction mixture was allowed to warm up at room temperature. After 2 h, Pd [(PPH3)] 2Cl2 (100 mg) and Cul (80 mg) and trimethylsilylacetylene (0.5 ml) were added again, and the reaction mixture was stirred overnight. Then, the reaction mixture was diluted with AcOEt and successively washed with a saturated aqueous solution of NH4CI and brine, dried over [MGS04,] filtered and concentrated. The crude residue was then purified by flash chromatography on silica gel (AcOEt/hexane: [5/95010/90)] to afford the title compound XXXI (9.05 g, 38.95 [MMOL,] 94% yield) as a yellow sticky [SOLID. 1H] NMR: (400 MHz, CDCl3) 8 [(PPM)] : AB system [(8A] = 7.67, AB = 7.22, JAB = 8.5 Hz, 4H), 3.63 (s, 3H), 0.00 (s, 9H).

The synthetic route of 619-42-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; METHYLGENE INC.; WO2004/35525; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 3196-23-4, 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. 3196-23-4, name is Methyl 1-bromocyclohexanecarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

a. Benzhydryl 2-(2-tritylaminothiazol-4-yl)-(Z)-2-(1-methoxycarbonylcyclohexyloxyimino)acetate Benzhydryl 2-(2-tritylaminothiazol-4-yl)-(Z)-2-(hydroxyimino)acetate (2.0 g) was treated with methyl 1-bromocyclohexane carboxylate as described in Example 5a to give the title compound (1.7 g, 69%) as a white solid, m.p. 180-182 C. (ethyl acetate/hexane). [Found: C: 73.73; H: 5.60; N: 5.69. C45 H41 N3 O5 S requires C: 73.45; H: 5.62; N: 5.71%] numax (KBr) 3406, 2945, 1751, and 1528cm-1, deltaH (CDCl3) 1.36 (5H, m), 1.72 (3H, m), 2.00 (2H, m), 3.69 (3H, s), 6.46 (1H, s), 6.71 (1H, s), 7.15 (1H, s), 7.29 and 7.34 (25H, m).

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

Reference:
Patent; Beecham Group P.L.C.; US4816452; (1989); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 34529-06-1, name is Dimethyl 3-aminophthalate, A new synthetic method of this compound is introduced below., Quality Control of Dimethyl 3-aminophthalate

To a stired solution of 3-amino-phthalic acid dimethyl ester (8.23 g, 39.32 mmol) in methylene chloride (200 ml) under a nitrogen atmosphere, 2-furaldehyde (8.14 ml, 98.30 mmol) and acetic acid (13.57 ml, 235.92 mmol) were added. The mixture was stirred for 5 minutes, followed by addition of sodium triacetoxyborohydride (25 g, 117.96 mmol). The reaction was sitirred overnight, washed with water (2¡Á200 ml), saturated aqueous sodium bicarbonate (2¡Á200 ml), and brine (200 ml), and dried over MgSO4. The solvent was evaporated in vacuo to give a brown oil (12.42 g), which was used directly without purification.

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; Muller, George W.; Man, Hon-Wah; US2006/25457; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 55666-42-7, A common heterocyclic compound, 55666-42-7, name is tert-Butyl 2-bromobenzoate, molecular formula is C11H13BrO2, 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.

tert-Butyl 2-bromobenzoate (800 mg, 3.11 mmol) and anhydrous THF (5 mL) were added to a dried flask under an argon atmosphere. The mixture was cooled to -78 C., and then 1 M sec-butyllithium (2.0 mmol) was added thereto, and the mixture was stirred for 20 minutes. 3,6-DiOTBDMS-Si-xanthone (40.0 mg, 0.0802 mmol) dissolved in anhydrous THF (5 mL) was slowly added to the mixture at the same temperature, and the mixture was brought to room temperature. The mixture was stirred at room temperature for 30 minutes, and then 2 N hydrochloric acid (10 mL) was added thereto, and the mixture was stirred for 20 minutes. The mixture was extracted with dichloromethane, and the organic layer was washed with brine, and dried over sodium sulfate. The solvent was removed, then trifluoroacetic acid (TFA, 3 mL) was added to the residue, and the mixture was stirred at room temperature for 1 hour. The solvent was removed, and then the residue was purified by HPLC to obtain 2-COOH TM (13.6 mg, 0.0358 mmol, yield 45%). (0205) 1H-NMR (300 MHz, CD3COCD3): delta 0.56 (s, 3H), 0.64 (s, 3H), 6.76 (dd, 2H J=2.9, 8.8 Hz), 6.83 (d, 2H, J=8.8 Hz), 7.23 (d, 2H J=2.9 Hz), 7.38 (d, 1H, J=7.3 Hz), 7.67 (td, 111, J=1.5, 7.3 Hz), 7.80 (td, 1H, J=1.5, 7.3 Hz), 7.94 (dd, 1H, J=1.5, 7.3 Hz) (0206) 13C-NMR (100 MHz, CD3COCD3): delta -1.4, 0.2, 91.1, 117.6, 121.1, 125.5, 126.3, 127.0, 129.3, 130.1, 135.1, 136.7, 138.2, 155.3, 157.7, 170.4 (0207) HRMS (ESI+): m/z Found 375.1018. calculated 375.1053 for [M+H]+ (-3.5 mmu)

The synthetic route of 55666-42-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE UNIVERSITY OF TOKYO; Nagano, Tetsuo; Hanaoka, Kenjiro; Koide, Yuichiro; Egawa, Takahiro; US9170266; (2015); B2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 773134-11-5, 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. 773134-11-5, name is Methyl 4-bromo-2,6-difluorobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

To a 50 mL round-bottom flask was added (1S,4S,5R)-5-[[4-cyclopropyl-l-(2,6- dichlorophenyl)-1H-pyrazol-5-yl]methoxy]-2-azabicyclo[2.2.1]heptane li (117 mg, 0.31 mmol, 1.00 equiv.), toluene (3 mL), methyl 4-bromo-2,6-difluorobenzoate (85 mg, 0.34 mmol, 1.10 equiv.), Ruphos precatalyst (53 mg, 0.06 mmol, 0.20 equiv.), Ruphos (29 mg, 0.06 mmol, 0.20 equiv.), and Cs2CO3 (303 mg, 0.93 mmol, 3.00 equiv.). The resulting mixture was heated at 110C overnight and concentrated under vacuum. The residue was purified by silica gel column chromatography eluting with ethyl acetate/petroleum ether (1 : 1) to give methyl 4-[(1S,4S,5R)-5- [[4-cyclopropyl-l-(2,6-dichlorophenyl)-1H-pyrazol-5-yl]methoxy]-2-azabicyclo[2.2.1]heptan-2- yl]-2,6-difluorobenzoate 3a (80 mg, 47%) as a light yellow solid.

The chemical industry reduces the impact on the environment during synthesis Methyl 4-bromo-2,6-difluorobenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ARDELYX, INC.; CHAO, Jianhua; (231 pag.)WO2019/55808; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 7149-03-3, A common heterocyclic compound, 7149-03-3, name is Ethyl 4-amino-3-bromobenzoate, molecular formula is C9H10BrNO2, 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.

Compound 11b (11.8 g, 48.34 mmol) was dissolved in concentrated hydrochloric acid (60.43 mL, 12N) at -10C, then a solution of sodium nitrite (4.00 g, 58.01 mmol) in water (300 mL) was added dropwise. The resulting reaction solution was reacted at 0C for 0.5 hour, and added at -10C in portions to another reaction vessel containing cuprous chloride (1.44 g, 14.50 mmol) and liquid sulfur dioxide (9.29 g, 145.03 mmol). . The resulting reaction solution was reacted at 0C for 0.5 hours. After extraction with ethyl acetate (100 mL¡Á3), the organic phase was washed with saturated brine (100 mL¡Á3), dried over anhydrous sodium sulfate, filtered, and concentrated to give compound 11c (14.00 g).

The synthetic route of 7149-03-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhengda Tianqing Pharmaceutical Group Co., Ltd.; Nanjing Mingde Drug Discovery Co., Ltd.; Yao Yuanshan; Chen Bin; Chen Yuan; Li Ao; Xu Ran; Huang Zhensheng; Tian Dongdong; Li Hongwei; Yang Chengshuai; Li Jian; Chen Shuhui; (26 pag.)CN107987072; (2018); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 1014645-87-4,Some common heterocyclic compound, 1014645-87-4, name is Methyl 4-(1-aminocyclopropyl)benzoate hydrochloride, molecular formula is C11H14ClNO2, 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 (3R)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid (syn-anti diastereoisomer mixture 10/2) (D27) (3.06 g, 13.5 mmol) in dry DMF (15 ml) under N2 atmosphere HOBT.H2O (2.06 g, 13.46 mmol), EDC.HCl (3.87 g, 20.20 mmol), methyl 4-(1-aminocyclopropyl)benzoate hydrochloride (3.06 g, 13.46 mmol) and TEA (4.7 ml, 33.7 mmol) were added in sequence. The mixture was stirred for 2 hrs at RT, then the solvent was evaporated in vacuo and the residue taken up in AcOEt (500 ml), washed twice with water (50 ml), dried over Na2SO4 and evaporated to afford a residue which was loaded on a SNAP-Si cartridge (100 g) and eluted with a mixture DCM/AcOEt from 10/0 to 9/1. Collected fractions after solvent evaporation afforded the two diastereoisomer (D73a) (2.55 g) and (D73b) (880 mg).(D73a) (syn diastereoisomer)MS: (ES/+) m/z: 401.4 [MH+] C22H28N2O5 requires 400.201H NMR (400 MHz, DMSO-d6) delta (ppm): 8.70 (s, 1H), 7.90-7.76 (m, 2H), 7.34-7.19 (m, 2H), 4.52-4.35 (m, 1H), 3.84 (s, 3H), 3.43-3.32 (m, 1H), 2.67-2.39 (m, 1H), 1.88-1.74 (m, 1H), 1.52-1.33 (m, 10H), 1.27-1.12 (m, 4H), 1.09-0.92 (m, 1H), 0.66-0.53 (m, 1H).(D73b) (anti diastereoisomer)MS: (ES/+) m/z: 401.4 [MH+] C22H28N2O5 requires 400.201H NMR (400 MHz, DMSO-d6) delta (ppm): 8.69-8.52 (s, 1H), 7.90-7.73 (m, 2H), 7.35-7.19 (m, 2H), 3.93-3.75 (m, 4H), 3.36-3.30 (m, 1H), 2.35-2.19 (m, 1H), 2.12-2.02 (m, 1H), 1.90-1.74 (m, 1H), 1.47-1.30 (m, 9H), 1.25-1.07 (m, 4H), 0.73 (td, J=5.4, 8.8 Hz, 1H), 0.39 (br. s., 1H).

The synthetic route of 1014645-87-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Borriello, Manuela; Pucci, Sabrina; Stasi, Luigi Piero; Rovati, Lucio; US2015/87626; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 54535-22-7, These common heterocyclic compound, 54535-22-7, name is Diethyl 2-((phenylamino)methylene)malonate, 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.

A I L three-necked flask fitted with a mechanical stirrer was charged with 2- phenylaminomethylene-malonic acid diethyl ester (26.3 g, 0.100 mol), polyphosphoric acid (270 g) and phosphoryl chloride (750 g). The mixture was heated to 70 C and stirred for 4 h. The mixture was cooled to room temperature and filtered. The residue was treated with aqueous Na2C03 solution, filtered, washed with water and dried. 4- Hydroxyquinoline-3-carboxylic acid ethyl ester was obtained as a pale brown solid (15.2 g, 70%). The crude product was used in next step without further purification.

The synthetic route of 54535-22-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; HASELTINE, Eric L.; MOSKOWITZ, Samuel; ROBERTSON, Sarah; WALTZ, David; (169 pag.)WO2019/18395; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics