Month: March 2021

Synthetic Route of 181140-34-1, 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. 181140-34-1 name is (R)-(-)-N-(2,3-Epoxypropyl)phthalimide, 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: Compounds 3-7 have been synthesized using a procedure originallyreported by Roehrig et al.16 Chiral amine or amino alcohol(0.6 mmol, 1.2 equiv) in 10 mL isopropanol was added to the solutionof (R)-N-(2,3-epoxypropyl)phthalimide (102 mg, 0.50 mmol)in 10 mL of isopropanol at in an ice bath and stirred for 1 h. thenrefluxed for 12 h. The reaction monitored by TLC. Solvent was removed by rotary evaporator under reduced pressure after completionof the reaction.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (R)-(-)-N-(2,3-Epoxypropyl)phthalimide, and friends who are interested can also refer to it.

Reference:
Article; Karakaplan, Mehmet; Jameel, Basam; Tetrahedron Asymmetry; vol. 27; 14-15; (2016); p. 597 – 602;,
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Related Products of 114041-16-6, A common heterocyclic compound, 114041-16-6, name is 5,6-Dimethoxyisoindoline, molecular formula is C10H13NO2, 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 solution of 5,6-dimethoxyisoindoline 10e (0.12 g, 0.69 mmol) in acetic acid (1.4 mL) is vigorously stirred while cooling with a cold-water bath. Sulfuryl chloride (0.073 mL, 0.90 mmol) is added drop-wise. The resulting mixture is then warmed to room temperature and stirred for 3 h. The reaction mixture is diluted with diethyl ether (1.4 mL) and stirred for 30 minutes. The mixture is filtered and the solid isolated to give a mixture of the HCl salt of product 10h (0.134 g, 76%) and starting material (3:1 ratio respectively).

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; Gladius Pharmaceuticals, Inc.; SUTTON, Larry D.; ZAMBONI, Robert; BUREAU, Patrick; HASSANPOUR, Avid; MAMANI LAPARRA, Laura; VIDAL, Marc; WOO, Simon; ZHOU, Nancy; KEENAN, Richard M.; (127 pag.)US2019/100534; (2019); 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. 2307-00-8, name is 5-Amino-2-methylisoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Formula: C9H8N2O2

A mixture of 4-Bromo-N-cyclopropylmethyl-2-trifluoromethyl-benzenesulfonamide (150 mg), Pd(OAc)2 (9.5 mg), BINAP (26 mg)5cesium carbonate (164 mg) and 5- Amino-2-methyl-isoindole-l,3-dione (148 mg) in 15 ml toluene was reflaxed for 12 hours. The reaction mixture was eluted through a silica bed with Toluene and then with PE: EtOAc (1:1). The toluene fraction was discarded and the solvent of the PE: EtOAc fraction was removed under reduced pressure. The crude product was purified by Combiflash (linear gradient PE – THF). Yield 83 mg, 43 %.1H NMR (300 MHz, CDC13, rt) delta 0.13 (m, 2H5 CH2), 0.49 (m, 2H, CH2), 0.89 (m, IH, CH), 2.87 (t, broad, 2H, J= 7.2 Hz5 CH2), 3.18 (s, 3H5 CH3), 4.72 (t, broad, IH, NH), 6.75 (s, broad, IH, NH)5 6.98 (s, IH5 ArH)5 7.37 (dt, J= 8.1, J= 2.7, IH5 ArH)5 7.489 (d, IH5 J= 2.1, ArH)5 7.579 (d, IH5 J= 1.8, ArH)5 7.81 (d, IH5 J= 8.I5 ArH), and 8.14 (d, 2H, J= 8.7Hz5 ArH).MS: m/z 454.1 (M+)

The synthetic route of 2307-00-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMOS CORPORATION; WO2008/75353; (2008); A1;,
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These common heterocyclic compound, 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, 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. Safety of 5-Bromo-1-methylindoline-2,3-dione

General procedure: DABCO (0.112 g, 1.00 mmol) was added to a solution of 2a (0.08 g, 0.5 mmol), phenol (0.094 g, 1.00 mmol) and 1a (0.147 g, 1.00 mmol) in acetonitrile (0.5 mL), and the reaction was kept for 2 days. The reaction mixture was then directly subjected to column chromatography (EtOAc/Hexane, 3:10) to obtain the product 3aa as a yellow solid (0.142 g) at 92% yield.

The synthetic route of 5-Bromo-1-methylindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Singh, Radhey M.; Bharadwaj, Kishor Chandra; Tiwari, Dharmendra Kumar; Beilstein Journal of Organic Chemistry; vol. 10; (2014); p. 2975 – 2980;,
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Related Products of 20870-79-5, The chemical industry reduces the impact on the environment during synthesis 20870-79-5, name is 5-Nitroindolin-2-one, I believe this compound will play a more active role in future production and life.

5-Amino-2-oxindole 5-Nitro-2-oxindole (6.3 g) was hydrogenated in methanol over 10% palladium on carbon to give 3.0 g (60% yield) of the title compound as a white solid.

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, 5-Nitroindolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sugen, Inc.; US6350754; (2002); B2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, A new synthetic method of this compound is introduced below., Formula: C9H7NO3

General procedure: Intermediates (7) (140 mg, 1.2 equiv.), PyBOP (1.2 equiv.) and DIPEA (1.5 equiv.) were added toDMF and stirred at room temperature for 20 min. Then, intermediates (4a-d) (1.0 equiv.) was addedand stirred at room temperature for 4 h. After completion of the reaction, the reaction mixture wasquenched with saturated NaCl solution (25 mL). The aqueous phase was extracted with DCM (25 ¡Á3 mL). The DCM layer was combined and washed with brine solution (25 ¡Á 3 mL). The organic layerwas dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. Afterconcentration, the crude product was purified by silica gel column chromatograph using a methanolin DCM gradient (DCM: methanol= 60:1-5:1) yielded compounds 8i-l.

The synthetic route of 102359-00-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Guo, Yan; Yang, Hongyu; Huang, Zhongwei; Tian, Sen; Li, Qihang; Du, Chenxi; Chen, Tingkai; Liu, Yang; Sun, Haopeng; Liu, Zongliang; Molecules; vol. 25; 3; (2020);,
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Synthetic Route of 110568-64-4, These common heterocyclic compound, 110568-64-4, name is 6-Nitroisoindolin-1-one, 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 3: 5-aminoisoindolin-1-oneIron powder (2.51 g, 45 mmol), water (0.97 ml) and HCl (37percent, 0.74 ml), were added to a stirred suspension of the 5-nitroisoindolin-1-one (800 mg, 4.5 mmol) from step 2 of this example in EtOH (11.2 ml). The mixture was heated at 95 ¡ãC for 2h. Ammonia (7N in MeOH) was added (ImL) to make the pH of the mixture alkaline. The mixture was filtered to removed undissolved solids and the filter cake washed with EtOH (2×40 ml). The filtrate and organic washes were combined and concentrated in vacuum to give the titled compound.

Statistics shows that 6-Nitroisoindolin-1-one is playing an increasingly important role. we look forward to future research findings about 110568-64-4.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WOOD, Harold, B.; ADAMS, Alan, D.; SZEWCZYK, Jason, W.; ZHANG, Yong; YANG, Meng; WO2011/19538; (2011); A1;,
Indoline – Wikipedia,
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Synthetic Route of 50727-04-3, A common heterocyclic compound, 50727-04-3, name is 5-Methoxyisoindoline-1,3-dione, molecular formula is C9H7NO3, 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-bromo-5-trifluoromethylpyridine (224 mg, 1 mmol), triethylene diamine (224 mg, 2 mmol),4-methoxyphthalimide (354 mg, 2 mmol), potassium phosphate (434 mg, 2 mmol),N, N-dimethylacetamide (2 ml) was added to the dry reaction tube and suspended in an oil bath at 120 C for 24 h.After cooling the reaction system, 15 ml of water was added and the aqueous phase was extracted three times with 30 ml of ethyl acetate,The organic phases were combined and the solvent was evaporated under reduced pressure to give 338 mg of a colorless solid, 5-methoxy-2- (2-(4- (5-trifluoromethylpyridyl) 2-piperazinyl) 1-ethyl) isoindole-1,3-dione in a yield of 78%.

The synthetic route of 50727-04-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Yichun University; Zhu Qiming; Chen Mingwei; (20 pag.)CN106317021; (2017); A;,
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Synthetic Route of 6326-79-0, These common heterocyclic compound, 6326-79-0, name is 6-Bromoisatin, 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 the reaction vessel, 6-bromoisatin (10.0 g, 22 mmol) and 1N aqueous NaOH solution (48 mL) were added and the mixture was heated to 50C and stirred for 1 hour. The reaction solution was cooled to 0C, and a mixture of sodium nitrite (3.0 g, 22 mmol) and water (11 mL) was added slowly. Water (90 mL) and sulfuric acid (4.6 mL) were slowly added to the mixture at the same temperature and stirred. To the reaction mixture was added a mixture of tin chloride dihydrate (24.0 g, 53 mmol) and hydrochloric acid (40 mL) at 0 C, and the mixture was stirred at room temperature. The resulting solid was filtered, washed with water and dried to give the desired compound (8.53 g, 80% yield) as a yellow solid.

Statistics shows that 6-Bromoisatin is playing an increasingly important role. we look forward to future research findings about 6326-79-0.

Reference:
Patent; Korea Institute of Science and Technology; Sim Tae-bo; Noh Eun-ju; Yang Han-yong; (33 pag.)KR101936851; (2019); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 6780-38-7,Some common heterocyclic compound, 6780-38-7, name is 2-(1,3-Dioxoisoindolin-2-yl)acetyl chloride, molecular formula is C10H6ClNO3, 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 tert-butyl 3-amino-4-methylphenylcarbamate (0.667 g, 3 mmol), 2-(l,3-dioxoisoindolin-2-yl)acetyl chloride (0.671 g, 3.00 mmol) in DCM (10 mL) was added diisopropylethylamine (1.048 mL, 6.00 mmol). After stirring 25 C for 15 h, saturated aqueous sodium chloride (25 mL) was added and extracted with ethyl acetate (3 x 25 mL). The organic layers were combined, dried (MgSO4), filtered, and concentrated. The crude product was purified by silica gel chromatography (100% ethyl acetate) to give the title compound as a white solid (1.15 g, 2.81 mmol, 94% yield); 1H NMR (400 MHz, DMSO-d6) delta 9.70 (s, IH), 9.29 (s, IH), 7.91 – 7.99 (m, 2H), 7.83 – 7.91 (m, 2H), 7.56 (s, IH), 7.13 (d, J= 8.20 Hz, IH), 7.07 (d, J- 8.20 Hz, IH), 4.45 (s, 2H), 2.11 (s, 3H), 1.45 (s, 9H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(1,3-Dioxoisoindolin-2-yl)acetyl chloride, its application will become more common.

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; WO2009/89042; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem