Category: 129487-92-9

Safety of tert-Butyl 5-aminoindoline-1-carboxylate,Chemistry involves the study of all things chemical – chemical processes, chemical compositions and chemical manipulation – in order to better understand the way in which materials are structured, how they change and how they react in certain situations.

The 1-tert-butoxy-carbonyl-5-amino indoline (3g, 14mmol) dissolved in water (3 ml) in, cooling to-5-0 C degrees, dropping sodium nitrite (1.16g, 16 . 8mmol) of water (3 ml) solution, 0 C stirring for 30 minutes, a diazo reaction liquid obtained, the spare; sodium acetate (2.64g, 32 . 2mmol) dissolved in water (3 ml) in, by adding 2-chloro acetyl ethyl acetate (2.3g, 14 . 0mmol) second grade fat of the acetic acid (5 ml) solution, cooled to 0 C, spare the dropping of a diazo reaction solution, 0 C reaction 1 hour. Adding water to the reaction solution (50 ml), ethyl acetate (50 ml × 3) extraction, combined organic phase, the organic phase with water (50 ml × 2) washing, dry anhydrous sodium sulfate, concentrated, the title compound ethyl 2-chloro-2-(2-(indolin-5-yl)hydrazono)acetate (25B), yellow solid (1.2g, yield 32%).

According to the analysis of related databases, 129487-92-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SICHUAN HAISCO PHARMACEUTICAL CO LTD; WEI, YONGGANG; QIU, GUANPENG; LEI, BAILIN; LU, YONGHUA; (120 pag.)CN104395312; (2016); B;,
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Redox catalysis has been broadly utilized in electrochemical synthesis. The appropriate choice of redox mediator can avoid electrode passivation and overpotential, which strongly inhibit the efficient activation of substrates in electrolysis., Recommanded Product: 129487-92-9

To a solution of 300mg (1.28mmol) of the compound obtained in the Manufacturing Example 2 in 10mL of anhydrous dichloromethane were added 191muL (2.69mmol) of acetyl chloride and 375muL (2.69mmol) of triethylamine, and the mixture was stirred for 1 hour at room temperature. Then, water was added to the reaction mixture and the mixture was extracted with dichloromethane. The organic layer was dried over with anhydrous sodium sulfate and removed under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate = 1/1 to 1/2) to give 370mg (quantitative) of the title compound.

As always, wish you can browse a selection of our May HOT articles below about tert-Butyl 5-aminoindoline-1-carboxylate.

Reference:
Patent; Daiichi Asubio Pharma Co., Ltd.; EP1775298; (2007); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 129487-92-9, A common heterocyclic compound, 129487-92-9, name is tert-Butyl 5-aminoindoline-1-carboxylate, molecular formula is C13H18N2O2, 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 5-aminodihydroindole-1-carboxylic acid tert-butyl ester (200 mg, 0.77 mmol) and 4,6-dichloropyridazine-3-carboxylic acid methyl ester 1a (200 mg, 0.97 mmol) were dissolved in ethanol ( 10mL),It was then heated to 90 C in a sealed tube and stirred for 12 hours.After cooling to room temperature, the solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography (petroleum ether / ethyl acetate = 1/1).The target product 5-((6-chloro-3- (methoxycarbonyl) pyridazin-4-yl) amino) dihydroindole-1-carboxylic acid tert-butyl ester 35a (200 mg, white solid) was obtained,Yield: 58%.

The synthetic route of 129487-92-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Beijing Nuochengjianhua Pharmaceutical Technology Co., Ltd.; Chen Xiangyang; Pang Yucheng; (142 pag.)CN110818641; (2020); A;,
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. 129487-92-9, name is tert-Butyl 5-aminoindoline-1-carboxylate, A new synthetic method of this compound is introduced below., category: indolines-derivatives

Part A. To the product (1.0 g, 4.2 mmol) from Example 2, Part B, was added N,N-dimethylglycine (490 mg, 4.7 mmol), triethylamine (1.80 ml, 13 mmol), and DMF (30 mL). To this mixture was added benzotriazol-1-yloxytripyrrolidino-phosphonium hexafluorophosphate (2.2 g, 4.3 mmol). After 10 min, the clear yellow solution was poured into EtOAc (80 mL) and washed with H2O (2×50 mL). The organic layer was washed with brine, dried over Na2SO4, and filtered. The resulting residue was purified by radial chromatography (5% MeOH in CH2Cl2) to afford tert-butyl 5-[(N,N-dimethylglycyl) amino]-1-indolinecarboxylate (1.50 g, 110%) containing a small amount of DMF. LC/MS (ESI+): 320.1 (M+H)+.

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; Pinto, Donald J.P.; Han, Wei; Hu, Zilun; Qiao, Jennifer; US2003/232804; (2003); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 129487-92-9,Some common heterocyclic compound, 129487-92-9, name is tert-Butyl 5-aminoindoline-1-carboxylate, molecular formula is C13H18N2O2, 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.

Part H. To tert-butyl-5-amino-1-indolinecarboxylate (1.90 g, 8.2 mmol) was added 5-bromovaleryl chloride (1.4 mL, 9.0 mmol) and 18 mL of THF. After stirring for 5 min at rt under N2, potassium tert-butoxide (9 mL, 9 mmol; 1.0 M in THF) was added in one portion, and the resulting brown solution was stirred under N2 for 30 min. A second portion of potassium tert-butoxide (9 mL) was added, and the resulting brown suspension was stirred for 15 min. An additional 0.10 mL-portion of 5-bromovaleryl chloride and a 4.5 mL-portion of potassium tert-butoxide were added, and the mixture was stirred for 30 min. The reaction was then poured into H2O (80 mL). The aqueous layer was washed with EtOAc (3*50 mL), and the combined organic layers were washed with brine, dried over Na2SO4, and filtered. The filtrate was concentrated and the resulting residue was purified by radial chromatography (50% EtOAc in hexanes) to afford tert-butyl 5-(2-oxo-1-piperidinyl)-1-indolinecarboxylate as a pink solid (1.30 g, 50%). LRMS (AP+): 317.2 (M+H)+. 1H NMR (CDCl3) delta7.40-7.80 (br m, 1H), 7.01 (s, 1H), 6.97 (d, 1H), 3.94 (t, 2H), 3.55 (br m, 2H), 3.09 (t, 2H), 2.49 (br m, 2H), 1.91 (br m, 4 H), 1.52 (s, 9H).

The synthetic route of 129487-92-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pinto, Donald J.P.; Quan, Mimi L.; Orwat, Michael J.; Li, Yun-Long; Han, Wei; Qiao, Jennifer X.; Lam, Patrick Y.S.; Koch, Stephanie L.; US2003/191115; (2003); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 129487-92-9, name is tert-Butyl 5-aminoindoline-1-carboxylate, molecular formula is C13H18N2O2, 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. Computed Properties of C13H18N2O2

To a solution of 2-bromo-3-((4-fluorophenyl)ethynyl)pyridine (intermediate 42, 340 mg, 1.23inmol) in anhydrous toluene (15 rnL) was added Pd2(dba)3 (113 mg, 0.123 mmol), XPhos (117 rng,0.246 mmoi) and potassium tert-butoxide (414 mg, 3.69 mrnol) under N2. After 10 mm, tert-butyl5-aminoindoline- I -carboxylate (Intermediate 12, 519 mg, 1.75 mmol) was added and the mixturewas stirred at 20 C for 10 mm, Then, the mixture was heated at 100 C for 3hr, EtOAc and waterwere added. The organic phase was separated and dried (Mg504), filtered and concentrated.Purification IFCC. Si02 0:100 to 30:70, EtOAc/heptane) afforded the title compound (330 mg,62%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 129487-92-9, its application will become more common.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BERRY, Cynthia G.B.; CHEN, Gang; JOURDAN, Fabrice Loic; LEBOLD, Terry Patrick; LIN, David Wei; PENA PINON, Miguel Angel; RAVULA, Suchitra; SAVALL, Bradley M.; SWANSON, Devin M.; WU, Dongpei; ZHANG, Wei; AMERIKS, Michael K.; (407 pag.)WO2016/176460; (2016); A1;,
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. 129487-92-9, name is tert-Butyl 5-aminoindoline-1-carboxylate, A new synthetic method of this compound is introduced below., COA of Formula: C13H18N2O2

Part H. To tert-butyl-5-amino-1-indolinecarboxylate (1.90 g, 8.2 mmol) was added 5-bromovaleryl chloride (1.4 mL, 9.0 mmol) and 18 mL of THF. After stirring for 5 min at rt under N2, potassium tert-butoxide (9 mL, 9 mmol; 1.0 M in THF) was added in one portion, and the resulting brown solution was stirred under N2 for 30 min. A second portion of potassium tert-butoxide (9 mL) was added, and the resulting brown suspension was stirred for 15 min. An additional 0.10 mL-portion of 5-bromovaleryl chloride and a 4.5 mL-portion of potassium tert-butoxide were added, and the mixture was stirred for 30 min. The reaction was then poured into H2O (80 mL). The aqueous layer was washed with EtOAc (3*50 mL), and the combined organic layers were washed with brine, dried over Na2SO4, and filtered. The filtrate was concentrated and the resulting residue was purified by radial chromatography (50% EtOAc in hexanes) to afford tert-butyl 5-(2-oxo-1-piperidinyl)-1-indolinecarboxylate as a pink solid (1.30 g, 50%). LRMS (AP+): 317.2 (M+H)+. 1H NMR (CDCl3) delta 7.40-7.80 (br m, 1H), 7.01 (s, 1H), 6.97 (d, 1H), 3.94 (t, 2H), 3.55 (br m, 2H), 3.09 (t, 2H), 2.49 (br m, 2H), 1.91 (br m, 4H), 1.52 (s, 9H).

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; Bristol-Myers Squibb Company; Pinto, Donald J.P.; Quan, Mimi L.; Orwat, Michael J.; Li, Yun-Long; Han, Wei; Qiao, Jennifer X.; Lam, Patrick Y.S.; Koch, Stephanie L.; (132 pag.)US2017/50964; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 129487-92-9, name is tert-Butyl 5-aminoindoline-1-carboxylate, 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. name: tert-Butyl 5-aminoindoline-1-carboxylate

A mixture of 2-isopropoxy-4-methylbenzoic acid (2.57 g), tert-butyl 5-AMINO-1-INDOLINECARBOXYLATE (3.41 g), 1- hydroxybenzotriazole hydrate (2.13 g) and 1- [3- (dimethylamino) PROPYL]-3-ETHYLCARBODIIMIDE (2.16 g) in N, N- dimethylformamide (30 ml) was stirred at ambient temperature overnight. The reaction mixture was poured into a mixture of ethyl acetate and water, and the organic layer was washed with brine and dried over magnesium sulfate. The solvent was concentrated in vacuo and the precipitate was collected by filtration to give tert-butyl 5- [ (2-ISOPROPOXY-4- methylbenzoyl) AMINO]-1-INDOLINECARBOXYLATE (4.82 g). 1H-NMR (DMSO-d6): 8 1. 38 (3H, d, J=6.02 Hz), 1.51 (9H, S), 2.36 (3H, s), 3.07 (2H, t, J=8.36 Hz), 3.91 (2H, t, J=8.36 Hz), 4.75-4. 80 (1H, m), 6.89 (1H, d, J=7.98 Hz), 7.04 (1H, s), 7.41 (1H, s), 7.63-7. 69 (2H, m), 7.71 (1H, d, J=7.98 Hz), 10.01 (1H, s)

The synthetic route of tert-Butyl 5-aminoindoline-1-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FUJISAWA PHARMACEUTICAL CO., LTD.; DAISO CO., LTD.; WO2004/39795; (2004); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 129487-92-9, name is tert-Butyl 5-aminoindoline-1-carboxylate, 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 129487-92-9, name: tert-Butyl 5-aminoindoline-1-carboxylate

13c) tert-butyl 5-(2-oxo-1,2-dihydro-3H-imidazo[4,5-b]pyridin-3-yl)-2,3-dihydro-1H-indole-1-carboxylate A mixture of tert-butyl 5-amino-2,3-dihydro-1H-indole-1-carboxylate (4.10 g), tert-butyl 2-chloropyridin-3-ylcarbamate (4.20 g), Pd2(dba)3 (0.48 g), Xantphos (0.608 g), sodium tert-butoxide (2.52 g) in 2-propanol (64 ml) and toluene (12 mL) was stirred at 90 C. for 40 h, and treated with water and extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated in vacuo. The residue was suspended in CH3CN and the precipitate was collected by filtration to give tert-butyl 5-(2-oxo-1,2-dihydro-3H-imidazo[4,5-b]pyridin-3-yl)-2,3-dihydro-1H-indole-1-carboxylate (1.64 g). The filtrate was evaporated and then the residue was chromatographed on silica gel eluting with AcOEt/Hexane=2/1 to afford second crop (1.4 g).MS (ESI+): [M+H]+353.3.

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; TANIGUCHI, Takahiko; YOSHIKAWA, Masato; MIURA, Kasei; HASUI, Tomoaki; HONDA, Eiji; IMAMURA, Keisuke; KAMATA, Makoto; KAMISAKI, Haruhi; QUINN, John F.; RAKER, Joseph; CAMARA, Fatoumata; WANG, Yi; US2011/319394; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 129487-92-9, name is tert-Butyl 5-aminoindoline-1-carboxylate, 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 129487-92-9, Recommanded Product: 129487-92-9

(2) tert-butyl 5-(3,5-dichloro-phenylsulphonylamino)-2,3-dihydro-indole-1 carboxylate; Mass spectrum (ESI+): m/z = 460 [M+NH4]+

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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; WO2008/113760; (2008); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem