Month: January 2021

Related Products of 3485-84-5,Some common heterocyclic compound, 3485-84-5, name is N-Vinylphthalimide, molecular formula is C10H7NO2, 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 20-mL, microwave reaction vessel was charged with (5-bromopyrimidin-4-yl)-(4-(trifluoromethyl)phenyl)methanol (560 mg, 1.68 mmol), 2-vinylisoindoline-1,3-dione (327.1 mg, 1.89 mmol), 2-(dicyclohexylphosphino)biphenyl (59.5 mg, 0.17 mmol), Pd(dba)2 (52.7 mg, 0.092 mmol), NEt3 (0.3 mL, 2.02 mmol), and DMF (4 mL). The mixture was purged with argon and heated in microwave synthesizer at 150 C. for 1 h. The reaction mixture was partitioned between water and EtOAc. The EtOAc layer was separated and aqueous layer was extracted again with EtOAc. The combined organic layers were washed with saturated NaHCO3, dried over Na2SO4, filtered, and concentrated in vacuo. The resulting residue was purified by silica gel chromatography (0-100% EtOAc in hexanes) to give 2-(2-(4-(4-(trifluoromethyl)benzoyl)pyrimidin-5-yl)ethyl) isoindoline-1,3-dione as a yellow solid. MS (ESI pos. ion) m/z: 426 (M+1). 1H NMR (400 MHz, CDCl3): delta 9.20 (s, 1H), 8.79 (s, 1H), 8.03 (d, J= 8.0 Hz, 2H), 7.67-7.74 (m, 6H), 3.98 (t, J= 6.3 Hz, 2H), 3.24 (t, J= 6.5 Hz, 2H). (E)-2-(2-(4-(hydroxy(4-(trifluoromethyl)phenyl)methyl)pyrimidin-5-yl)vinyl)isoindoline-1,3-dione was also collected as a yellow solid. MS (ESI pos. ion) m/z: 424 (M+1).

The synthetic route of 3485-84-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nishimura, Nobuko; Norman, Mark H.; Tamayo, Nuria; Tang, Phi; Bo, Yunxin Y.; US2009/82358; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 132898-96-5, 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. 132898-96-5, name is 2,3-Dioxoindoline-5-sulfonyl chloride belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Step 4: 5-({(2S)-2-[(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]pyrrolidin-1-yl}sulfonyl)-1H-indole-2,3-dione At 0 C., to a stirred suspension containing 5-chlorosulfonylisatin (1.76 g, 7.15 mmol) (J. Med. Chem, 44, 2014, 2001) and 2-[(2S)-pyrrolidin-2-ylmethyl]-1H-isoindole-1,3(2H)-dione hydrochloride (2.10 g, 7.83 mmol) in CH2Cl2 (36 mL) was added dropwise diisopropylethylamine (3.74 mL, 21.4 mmol). After the addition was complete, the reaction was stirred for 16 hours. The reaction was quenched with H2O (100 mL) and extracted with CH2Cl2. The combined organic extracts were dried (MgSO4) and concentrated. The crude product was purified on Biotage KP-Sil eluding with 15% acetone/CH2Cl2 to give 2.81 g, (90%) of the title compound. 1H NMR (DMSO-d6) yielded spectra consistent with the assigned structure.

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, 2,3-Dioxoindoline-5-sulfonyl chloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Wyeth; US2007/65898; (2007); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, This compound has unique chemical properties. The synthetic route is as follows., Formula: C9H7NO3

To a solution of 2-oxoindoline-5-carboxylic acid (200 mg, 1.12 mmol) in DMF (3 mL) was added HATU (644 mg, 1.69 mmol) and the reaction mixture was stirred for 30 min at room temperature. After being cooled to 0 C 1-cyclopropyl-4-methylpyrrolidin- 3-amine (174 mg, 1.24 mmol) and DIPEA (0.29 mL, 1.69 mmol) were added successively to the reaction mixture. The reaction was further stirred at room temperature for 2 hrs. Completion of the reaction was confirmed by TLC. After completion, water (30 mL) was added to reaction mixture and product was extracted with ethyl acetate (3 x 25 mL). The combined organic layer was washed with brine, and dried over sodium sulfate and concentrated under vacuum to get crude product which was purified by column chromatography. The desire compound started eluting at 4% methanol in DCM. Evaporation of the fractions afforded 70 mg of pure racemic compound as a mixture of cis : trans isomer. The cis and trans isomers were separated out using reverse-phase prep. HPLC using 0.1% TFA in ACN and 0.1% TFA in water as mobile phase. Lyophilization of pure fractions afforded the pure title compounds. The yields of the isomers were (18 mg (5.33%) and 23 mg (6.81%) a and LCMS of the isomers were: 1H NMR (400 MHz, MeOD): 7.7 97-6.95 (m, 1H), 4.15 (dd, J = 6 Hz, 1H), 3.60-3.58 (m, 1H), 3.51 (m , 1H), 3.18 (dd, J = 6 Hz, 1H), 2.82- 2.78 (m, 1H), 2.40-2.36 (t, J = 8.4 Hz, 1H), 2.25 2.21 (m, 1H), 1.21-1.20 (m, 3H), 0.53- 0.49 (m, 4H). LCMS (m/z): 300.25 [M+H]+. 1H NMR (400 MHz, MeOD): 7.78-7.76 (m, 2H), 6.98-6.96 (m, 1H), 4.68 (dd, J=5.2 Hz, 1H), 3.61-3.59 (m, 1H), 3.24 (dd, J=5.2 Hz, 1H), 3.12 (dd, J=7.6 Hz, 1H), 2.72 (dd, J=6.4 Hz, 1H), 2.59-2.55 (m, 1H), 2.45 (t, J= 9.2 Hz, 1H), 1.86-1.84 (m, 1H), 0.97-0.95 (m, 3H), 0.54-0.48 (m, 4H). LCMS (m/z): 300.25 [M+H]+.

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 102359-00-2.

Reference:
Patent; EPIZYME, INC.; FOLEY, Megan Alene Cloonan; KUNTZ, Kevin Wayne; MITCHELL, Lorna Helen; MUNCHHOF, Michael John; HARVEY, Darren Martin; (102 pag.)WO2016/40508; (2016); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 52537-00-5, name is 6-Chloro-2,3-dihydro-1H-indole belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 6-Chloro-2,3-dihydro-1H-indole

A mixture of tert-butyl 2-(4-amino-2-(4-bromo-l-methyl-lH-pyrazol-5-yl)rhohenoxy) ethylcarbamate (30 mg, 54 mumol) and 6-chloroindoline (8.3 mg, 54 mumol) in ImL of DMF was stirred at room temperature overnight. Then to the mixture was added 1 mL of 2M HCl. The mixture was stirred at room temperature overnight. The mixture was concentrated and the crude product was subjected to purification on HPLC. The proper fractions were collected and lyophilized to afford yellow oil in 20.1 % yield. LCMS m/z (%) = 492 (M+H 35Cl 79Br, 100). 1H NMR (400 MHz, MeOD) delta ppm 3.1 (m, 4 H), 3.7 (s, 3 H)3 4.1 (m, 3 H), 4.2 (m, 1 H), 6.8 (dd, J=7.6, 2.0 Hz, 1 H), 7.1 (d, 3=7.6 Hz, 1 H), 7.1 (d, J=9.1 Hz, 1 H), 7.3 (d, J=3.0 Hz, 1 H), 7.5 (s, 1 H), 7.6 (dd, J=9.1, 2.5 Hz, 1 H)5 7.8 (d, J=2.0 Hz, 1 H).

The synthetic route of 52537-00-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; WO2007/136703; (2007); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 6872-06-6, The chemical industry reduces the impact on the environment during synthesis 6872-06-6, name is 2-Methylindoline, I believe this compound will play a more active role in future production and life.

General procedure: 2-Methylindoline (400 mg, 3.0 mmol, 1.0 equiv) was dissolved in dry pyridine (10 mL). Methane sulfonyl chloride (480 mg, 4.2 mmol, 1.4 equiv) was added dropwise and the reaction mixture was stirred overnight at rt. Monitoring by HPLC and LCMS indicated that the reaction was completed. The solvent was evaporated under reduced pressure. A solution of HCl 1N (50 mL) and EtOAc (50 mL) were added. The organic layer was separated and the aqueous phase was extracted twice with EtOAc (2×50 mL). The combined organic phase was dried over Na2SO4 and the solvent was evaporated under reduced pressure to yield the pure product: 634 mg, 100 % yield.

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

Reference:
Article; Yacovan, Avihai; Ozeri, Rachel; Kehat, Tzofit; Mirilashvili, Sima; Sherman, Daniel; Aizikovich, Alex; Shitrit, Alina; Ben-Zeev, Efrat; Schutz, Nili; Bohana-Kashtan, Osnat; Konson, Alexander; Behar, Vered; Becker, Oren M.; Bioorganic and Medicinal Chemistry Letters; vol. 22; 20; (2012); p. 6460 – 6468;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 774-47-0, 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. 774-47-0, name is 5,6-Difluoroindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: TiCl4 (0.7 mL, 6 mmol)was added to a stirred suspension of Zn powder (0.78 g, 12 mmol) in freshlydistilled anhydrous THF (15 mL) at room temperature (rt) under a dry N2atmosphere. After completion of the addition, the mixture was refluxed for 2 h.The suspension of the low-valent titanium reagent thus-formed was cooled tort. A solution of isatin or its derivatives 1 or 3 (2 mmol) in THF (10 mL) wasadded dropwise. The mixture was stirred at room temperature for about 5 minunder N2. After this period, the thin layer chromatography (TLC) analysis of themixture showed the reaction completed. The reaction mixture was quenchedwith 3% HCl (15 mL) and extracted with CHCl3 (3 50 mL). The combinedextracts were washed with water (3 50 mL) and dried over anhydrousNa2SO4. After evaporation of the solvent under reduced pressure, the crudeproduct was purified by column chromatography (petroleum ether/ethylacetate = 5:1) to give the pure products 2 or 4.

The synthetic route of 5,6-Difluoroindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lin, Wei; Hu, Ming-Hua; Feng, Xian; Fu, Lei; Cao, Cheng-Pao; Huang, Zhi-Bin; Shi, Da-Qing; Tetrahedron Letters; vol. 55; 14; (2014); p. 2238 – 2242;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 1914-02-9, 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. 1914-02-9 name is 3,3-Dimethylindoline, 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 mixture of 3,3-dimethylindoline (105 mg, 0.713 mmol), ethyl 2-bromo-2-cyclopropylacetate (297 muL, 2.143 mmol), and potassium carbonate (300 mg, 2.171 mmol) in 2 mL CH3CN was stirred at 100C (oil bath) for 16 h. The mixture was extracted with 2 M HC1 and CH2C12. Organic phases were concentrated and residue was purified by preparative HPLC. Fractions containing product were partly concentrated and the residue was extracted with 1 M NaHC03and CH2C12. Organic phases were dried over MgS04, filtered, and concentrate to give ethyl 2-cyclopropyl-2-(3,3-dimethylindolin-l-yl)acetate (162 mg) as a brownish oil. LCMS m/z = 274.4 [M+l]+; NMR (400 MHz, CDC13) delta ppm 0.37-0.43 (m, 1H), 0.52-0.58 (m, 1H), 0.61-0.73 (m, 2H), 1.20 (t, J = 7.1 Hz, 3H), 1.26-1.34 (m, 7H), 3.33 (d, J = 9.4 Hz, 1H), 3.49 (d, J = 8.4 Hz, 1H), 3.61 (d, J = 8.4 Hz, 1H), 4.13 (q, J = 7.1 Hz, 2H), 6.30 (dd, J1= 7.5 Hz, J2= 0.8 Hz, 1H), 6.63-6.67 (m, 1H), 6.98-7.02 (m, 2H).

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

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; SEMPLE, Graeme; BEHAN, Dominic P.; FEICHTINGER, Konrad; GLICKLICH, Alan; GROTTICK, Andrew J.; KAM, Maria Matilde Sanchez; KASEM, Michelle; LEHMANN, Juerg; REN, Albert S.; SCHRADER, Thomas O.; SHANAHAN, William R.; WONG, Amy Siu-Ting; ZHU, Xiuwen; WO2015/66344; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 126674-93-9, name is 4,6-Difluoro-1H-indole-2,3-dione, belongs to indolines-derivatives 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 126674-93-9, Formula: C8H3F2NO2

[Reference Example 154] (0739) (0740) To the solution of 250 mg of 4,6-difluoro-1H-indole-2,3-dione in 3 mL of sulfuric acid, 109 muL of 60% nitric acid was added dropwise at -20C, and the resultant was stirred for 15 minutes. Water was added dropwise to the reaction mixture, followed by addition of ethyl acetate. The organic layer was separated, sequentially washed with a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (gradient elution with hexane:ethyl acetate) to give 180 mg of 4,6-difluoro-5-nitro-1H-indole-2,3-dione as a yellow solid. 1H-NMR (DMSO-d6) delta: 6.95 (1H, d, J = 10.6 Hz), 11.95 (1H, s) MS (ESI, m/z): 227 (M-H)-.

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, 4,6-Difluoro-1H-indole-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Toyama Chemical Co., Ltd.; FUJIFILM Corporation; TANAKA, Tadashi; KONISHI, Yoshitake; KUBO, Daisuke; FUJINO, Masataka; DOI, Issei; NAKAGAWA, Daisuke; MURAKAMI, Tatsuya; YAMAKAWA, Takayuki; EP2915804; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 3485-84-5, name is N-Vinylphthalimide, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C10H7NO2

General procedure: [{Rh(cod)}2(mu-Cl)2] (5 mumol), phosphorus ligand (20 mumol), and solvent (6.3 mL) were added to a pressure reactor (25 mL). After addition of formaldehyde (37 % in H2O, 6 mmol) and substrate (5 mmol) the reaction mixture was purged with nitrogen for several times and heated with stirring (1000 rpm) to the indicated reaction temperature. Once the desired temperature was achieved, H2 was introduced and the reaction mixture was stirred for the indicated reaction time. After cooling to room temperature the gas was released and the reaction mixture was again purged with nitrogen. Dodecane was added as an internal standard and brine in order to separate the phases. The organic phase was finally analyzed by GC.

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 3485-84-5.

Reference:
Article; Uhlemann, Marcus; Doerfelt, Stephan; Boerner, Armin; Tetrahedron Letters; vol. 54; 18; (2013); p. 2209 – 2211;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 6780-38-7, name is 2-(1,3-Dioxoisoindolin-2-yl)acetyl chloride belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 2-(1,3-Dioxoisoindolin-2-yl)acetyl chloride

General procedure: A solution of acyl chloride (1.2-5 mmol) in anhydrous benzene (5 mL) was added dropwise to a solution of diimine (1 mmol) and triethylamine (0.152-0.606 g, 1.5-6 mmol) in toluene (10 mL). The resulting mixture was stirred at 80 C under nitrogen for 4-16 h, which was determined by TLC monitoring. The reaction mixture was then diluted with CH2C12 (20 mL) and subsequently washed with saturated aqueous NaHCO3 solution (20 mL) and brine (2¡Á10 mL). After dried over anhydrous Na2SO4 and removal of solvent, the residue was purified via recrystallization with EtOAc or a mixture of EtOAc and hexanes or via flash column chromatography (silica gel, a mixture of hexanes and EtOAc as eluent) to afford the product.

The synthetic route of 6780-38-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Zhixin; Chen, Ning; Xu, Jiaxi; Tetrahedron; vol. 67; 50; (2011); p. 9690 – 9699;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem