Category: 102359-00-2

Electric Literature of 102359-00-2,Some common heterocyclic compound, 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, molecular formula is C9H7NO3, 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-Oxoindoline-5-carboxylic acid (0.214 g, 1.21 mmol), O-(BENZOTRIAZOL-L-YL)-N, N, N, N- TETRAMETHYLURONIUM TETRAFLUOROBORATE (0. 462 G, 1.44 mmol), 1-HYDROXYBENZOTRIAZOLE hydrate (0.194 g, 1.44 mmol) and N, N-diisopropylethylamine (0.3 ML, 1.71 mmol) were suspended in a mixture of acetonitrile (4 mL) and N, N-DIMETHYLFORMAMIDE (1 ML) and stirred at room temperature for 30 min. Benzylamine (0. 155 g, 1.45 mmol) was added and stirring was continued for 12 h. The solvent was removed in vacuo and the residue was separated between chloroform and a saturated aqueous sodium hydrogen carbonate solution. The aqueous layer was extracted with chloroform (3X30 mL). The combined organic layers were dried over sodium sulfate. Filtration and removal of the solvent in vacuo yielded the crude product which was purified on a silica gel column using a gradient chloroform/methanol, (100: 1 to 1: 1), as the eluent to give 0.104 g (30% yield) of the title compound as a solid : 1H NMR (DMSO-D6, 400 MHz) 8 10. 60 (s, 1 H), 8.85 (m, 1 H), 7.77 (m, 2 H), 7.29 (m, 4 H), 7.21 (m, 1 H), 6.85 (d, J = 11 HZ, 1 H), 4.45 (d, J = 6 Hz, 2 H), 3.52 (s, 2 H); MS (ES) TIZZY 267 (M++1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Oxoindoline-5-carboxylic Acid, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; WO2005/27823; (2005); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 102359-00-2, 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. 102359-00-2 name is 2-Oxoindoline-5-carboxylic Acid, 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.

1-[5-(Morpholine-4-carbonyl)-2-oxo-1,2-dihydro-indol-3-ylidenemethyl]-2,5,6,7-tetrahydro-pyrrolo[3,4-c]pyridin-4-one PyBOP (3.5 g, 6.72 mmol) was added to a mixture of 5-carboxy-2-oxindole (1 g, 5.6 mmol), morpholine (0.5 mL, 6.2 mmol) and triethylamine (2.0 mL, 14 mmol) in dichloromethane. After stirring at room temperature for 4 hours, the reaction was diluted with more dichloromethane, washed with saturated sodium bicarbonate and brine, dried and concentrated. The residue was purified by column chromatography to give 5-(morpholine-4-carbonyl)-1,3-dihydro-indol-2-one. 1NMR (300 MHz, DMSO-d6) delta 10.54 (br s, 1H, NH), 7.24 (m, 2H), 6.83 (d, J=7.6 Hz, 1H), 3.56 (m, 4H, 2*CH2), 3.49 (s, 2H, CH2), 3.47 (m, 4H, 2*CH2). MS APCI neg. m/z 245 [M+-1].

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Oxoindoline-5-carboxylic Acid, and friends who are interested can also refer to it.

Reference:
Patent; Tang, Peng Cho; Miller, Todd A.; Li, Xiaoyuan; Zhang, Ruofei; Cui, Jinrong; Huang, Ping; Wei, Chung Chun; US2002/42427; (2002); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, 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 102359-00-2, Recommanded Product: 2-Oxoindoline-5-carboxylic Acid

General procedure: A solution of 9a-d (2 mmol), EDCI (3 mmol) and HOBt (3 mmol) in dry DCM (20 mL) was stirred at 0C for 3.5 h. Then different substituted amines (2.2 mmol) and DIPEA (4 mmol) were added and the reaction was stirred at r.t. for another 1.5 h. The organic layer was washed with water and brine and dried over Na2SO4. Removal of the solvent gave a residue that was purified by column chromatography (silica gel, CH2Cl2-MeOH 100: 1 as an eluent) to furnish 10a-n as white solids.

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-Oxoindoline-5-carboxylic Acid, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Guo, Jing; Zhu, Mingyue; Wu, Tianxiao; Hao, Chenzhou; Wang, Kai; Yan, Zizheng; Huang, Wanxu; Wang, Jian; Zhao, Dongmei; Cheng, Maosheng; Bioorganic and Medicinal Chemistry; vol. 25; 13; (2017); p. 3500 – 3511;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 102359-00-2, A common heterocyclic compound, 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, 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.

General procedure: A solution of 9a-d (2 mmol), EDCI (3 mmol) and HOBt (3 mmol) in dry DCM (20 mL) was stirred at 0C for 3.5 h. Then different substituted amines (2.2 mmol) and DIPEA (4 mmol) were added and the reaction was stirred at r.t. for another 1.5 h. The organic layer was washed with water and brine and dried over Na2SO4. Removal of the solvent gave a residue that was purified by column chromatography (silica gel, CH2Cl2-MeOH 100: 1 as an eluent) to furnish 10a-n as white solids.

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; Guo, Jing; Zhu, Mingyue; Wu, Tianxiao; Hao, Chenzhou; Wang, Kai; Yan, Zizheng; Huang, Wanxu; Wang, Jian; Zhao, Dongmei; Cheng, Maosheng; Bioorganic and Medicinal Chemistry; vol. 25; 13; (2017); p. 3500 – 3511;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 102359-00-2, The chemical industry reduces the impact on the environment during synthesis 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, I believe this compound will play a more active role in future production and life.

Example 1 :(3Z)-3-[(4-{[2-(diethylamino)ethyl]carbamoyl}-3,5-dimethyl-1H-pyrrol- 2-yl)methylene]-2-oxoindoline-5-carboxylic acid (1)A mixture of 2-oxoindoline-5-carboxylic acid (0.708 g, 4 mmol), 3,5-dimethyl-4- (piperidin-1 -ylcarbonyl)-1 /-/-pyrrole-2-carbaldehyde (1 .030 g, 4.4 mmol) and piperidine (0.2 ml_) in EtOH (75 ml_) was refluxed for 8 h. The mixture was cooled down to room temperature to provide a precipitate which was filtered and washed with EtOH to provide the target compound 1 (0.980 g, 62.25%).NMR (300 MHz, DMSO-c/6) delta ppm: 13.52 (s,1 H), 12.5 (bs,1 H), 1 1 .19 (s,1 H), 8.37 (s,1 H), 7.78 (s,1 H), 7.77 (d,1 H), 6.96 (d,1 H), 3.43 (m,4H), 2.29 (s,6H), 1 .60 (bs,2H), 1 .47 (bs,4H); tR: 3.18 min, MS (ESI): m/z (M+H)+ 394; (M+HV392.

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-Oxoindoline-5-carboxylic Acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MAX-PLANCK-GESELLSCHAFT ZUR FOeRDERUNG DER WISSENSCHAFTEN E.V.; ULLRICH, Axel; FALCENBERG, Mathias; OeRFI, Zoltan; KERI, Gyoergy; OeRFI, Laszlo; HORVATH, Zoltan; SZOKOL, Balint; DOBOS, Judit; NEMES, Zoltan; WO2015/22437; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 102359-00-2, 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.

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 ×3 mL). The DCM layer was combined and washed with brine solution (25 × 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.N-((1-Benzylpiperidin-4-yl)methyl)-2-Oxoindoline-5-carboxamide (8i). 2-Oxoindoline-5-carboxylic acid(140 mg, 0.79 mmol), (1-Benzylpiperidin-4-yl)methanamine (135 mg, 0.66 mmol), PyBOP (412 mg,0.79 mmol), DIPEA(128 mg, 0.99 mmol), DMF (6 mL). White solid, m.p.:155-156 C, yield: 56%, 1HNMR (400 MHz, CD3OD) delta 7.73-7.68 (m, 2H), 7.53-7.42 (m, 5H), 6.91 (d, J = 8.1 Hz, 1H), 4.26 (s, 2H),3.44 (d, J = 12.5 Hz, 2H), 3.31 (s, 1H), 2.98 (t, J = 12.9 Hz, 2H), 1.97 (d, J = 13.6 Hz, 3H), 1.54 (q, J = 13.1,12.1 Hz, 2H). 13C NMR (101 MHz, CD3OD) delta 178.52, 168.90, 146.69, 130.99, 129.80, 129.40, 128.99,127.92, 127.60, 125.95, 123.42, 123.40, 108.97, 60.21, 51.86, 43.82, 42.11, 34.01, 26.82. HRMS (ESI):calcd. For C22H25N3O2 [M + H]+ 364.2020, found 364.2032.

The chemical industry reduces the impact on the environment during synthesis 2-Oxoindoline-5-carboxylic Acid. I believe this compound will play a more active role in future production and life.

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);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, 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 102359-00-2, COA of Formula: C9H7NO3

Into a 25-mL round-bottom flask was placed tert-butyl N-[1-[(1R,3r,5S)-3-amino- 8-azabicyclo[3.2.1]octane-8-sulfonyl]piperidin-4-yl]carbamate (200 mg, 0.51 mmol, 1.00 equiv), dichloromethane (5 mL), 2-oxo-2,3-dihydro-1H-indole-5-carboxylic acid (109 mg, 0.62 mmol, 1.20 equiv), EDCI (118 mg, 0.62 mmol, 1.20 equiv), and HOBT (104 mg, 0.77 mmol, 1.50 equiv). This was followed by the addition of TEA (260 mg, 2.57 mmol, 4.99 equiv) dropwise with stirring at 0oC. The resulting solution was stirred for 14 h at 20oC. The reaction mixture was then diluted with 10 mL of dichloromethane and was washed with 2×5 mL of brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was chromatographed on a silica gel column with ethyl acetate/petroleum ether (1:1). This resulted in 243 mg (86%) of tert- butyl N-[1-[(1R,3r,5S)-3-(2-oxo-2,3-dihydro-1H-indole-5-carboxamido)-8- azabicyclo[3.2.1]octane-8-sulfonyl]piperidin-4-yl]carbamate as a off-white solid

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Epizyme, Inc.; Poley, Megan Allen Clunan; Kunz, Kevin Wayne; Mills, James Edward John; Mitchell, Lona Helen; munckhof, Michael John; Harvey, Darren Martin; (303 pag.)KR2017/45749; (2017); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Recommanded Product: 102359-00-2

Prepared from 2-oxoindoline-5-carboxylic acid (500.0 mg, 2.87 mmol), conc. HCl (1.0 mL), AcOH (6.0 mL) and 3,5-dichloro-4-hydroxybenzaldehyde (536.7 mg, 2.87 mmol), 95 oC, 16 h. Yield = 640.0 mg, 65% (E/Z mixture). Major isomer: 1H NMR (DMSO-d6, 400 MHz) delta 10.9 (s, 1H), 8.2 (s, 1H), 7.88 (d, J = 1.7, 8.4 Hz), 7.80 (s, 2H), 7.57 (s, 1H), 6.97 (s, 8.0 Hz, 1H); MS (ES) m/z 384.0 [M+H]+ LCMS RT = 0.83 min (1 min method).

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

Reference:
Article; Dumas, Megan E.; Chen, Geng-Yuan; Kendrick, Nicole D.; Xu, George; Larsen, Scott D.; Jana, Somnath; Waterson, Alex G.; Bauer, Joshua A.; Hancock, William; Sulikowski, Gary A.; Ohi, Ryoma; Bioorganic and Medicinal Chemistry Letters; vol. 29; 2; (2019); p. 148 – 154;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 102359-00-2, The chemical industry reduces the impact on the environment during synthesis 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, I believe this compound will play a more active role in future production and life.

2-Oxoindoline-5-carboxylic acid (0.470 g, 2.66 mmol), O-(benzotriazol-1-yl)-N,N,N’,N’- TETRAMETHYLURONIUM TETRAFLUOROBORATE (1. 010 g, 3.15 mmol), 1-hydroxybenzotriazole hydrate (0.417 g, 3.09 mmol) and N, N-diisopropylethylamine (0.7 ML, 4.0 mmol) were suspended in ACETONITRILE/N-DIMETHYLFORMAMIDE, (10 mL: 2 mL), and stirred at room temperature for 30 min. 2-Methoxyethanamine (0.516 g, 6.88 mmol) was added and stirring was continued for 2 h. Saturated aqueous sodium hydrogencarbonate was added (10 mL) and the solvents were removed M vacuo. The residue was purified on a silica gel column using a gradient chloroform/methanol, (100: 1 to 1: 1), as the eluent to give 0.355 g (57% yield) of the title compound as a solid : 1H NMR (DMSO-DE, 400 MHz) 8 10.59 (s, 1 H), 8.31 (m, 1 H), 7.72 (d, J = 7 Hz, 1 H), 7.71 (s, 1 H), 6.83 (d, Y= 8 HZ, 1 H), 3.51 (s, 2 H), 3.42 (m, 2 H), 3.39 (m, 2 H), 3.24 (s, 3 H); MS (ES) TIL/Z 235 (M++1).

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-Oxoindoline-5-carboxylic Acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; WO2005/27823; (2005); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, 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. Recommanded Product: 2-Oxoindoline-5-carboxylic Acid

To A NN-DIMETHYLFORMAMIDE/ACETONITRILE, (2 mL: 10 mL), mixture containing ethyldiisopropylamine (0.52 ML, 3 mmol) was added 2-oxoindoline-5-carboxylic acid (0.354 g, 2.0 mmol; described in: Sun L. et al. J. MED. Chem. 2000, 43 (14), 2655:), O- (BENZOTRIAZOL-1-YL)-N, N, N, N-TETRAMETHYLURONIUM tetrafluoroborate (0.77 g, 2.4 mmol) and 1-HYDROXYBENZOTRIAZOLE hydrate (0.324 g, 2.4 mmol) and stirred for 5 min at room temperature. Thereafter, 2- (AMINOMETHYL) pyridine (0.562 g, 5.2 mmol) was added and the resulting reaction mixture was stirred for 90 min followed by addition of a saturated aqueous NAHCO3 solution (10 ML). The solvents were removed in vacuo and 0.364 g (68% yield) of the title product was obtained as a white solid after purification on a silica gel column using chloroform/methanol, (9: 1), as the eluent : 1H NMR (DMSO-d6, 400 MHz) 8 10. 66 (s, 1 H), 8.96 (t, 7= 5. 6 HZ, 1 H), 8.55 (d, J = 4.4 Hz, 1 H), 7. 85 (d, J = 8. 0 HZ, I H), 7.83 (s, 1 H), 7. 78 (t, J = 7.6 Hz, 1 H), 7.34 (d, J = 8.0 Hz, 1 H), 7.29 (t, J= 6. 4 Hz, 1 H), 6.92 (d, J = 8.0 Hz, 1 H), 4.59 (d, J = 6.0 Hz, 2 H), 3. 58 (s, 2 H); MS (EI) MLZ 268 (M++1).

The synthetic route of 2-Oxoindoline-5-carboxylic Acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2005/27823; (2005); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem