Category: 172078-33-0

172078-33-0, name is Indolin-5-ol, 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. Application In Synthesis of Indolin-5-ol

Example 40 5-(6-(5-hydroxyindoline-1-carbonyl)pyrimidin-4-ylamino)-1,3-dihydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-2′(1’H)-one 0.15 g (0.37 mmol) 6-(2′-oxo-1,1′,2′,3-tetrahydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-5-ylamino)pyrimidine-4-carboxylic acid hydrochloride, 50 mg (0.37 mmol) 2,3-dihydro-1H-indol-5-ol, 150 muL (0.87 mmol) DI PEA and 0.13 g (0.41 mmol) TBTU in 1.8 mL DMF were stirred overnight at RT. The purification was carried out by preparative HPLC-MS. The product-containing fractions were combined and lyophilised. Yield: 44 mg (23% of theory) ESI-MS: m/z=491 (M+H)+ Rt (HPLC-MS): 1.33 min (method C)

The synthetic route of 172078-33-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2011/21500; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 172078-33-0, These common heterocyclic compound, 172078-33-0, name is Indolin-5-ol, 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 1E (100 mg, 423 mmol), compound 24A (63 mg, 465 mmol) and cesium carbonate (303 mg, 930mmol) were added to NMP (1 mL). The reaction solution was heated to 120 C and stirred for 2 hours, and then thereaction was quenched with water, and extracted with ethyl acetate (3 x 10 ml). The organic layer was washed withsaturated NaCl solution, dried over anhydrous sodium sulfate, filtered and evaporated to dryness. The residue waschromatographed on a silica gel plate (dichloromethane/methanol = 10: 1, Rf = 0.2) and purified to give compound 24B(yellow solid, 80 mg, 57%).LCMS (ESI) m/z: 336.1(M+1)+

Statistics shows that Indolin-5-ol is playing an increasingly important role. we look forward to future research findings about 172078-33-0.

Reference:
Patent; GUANGDONG ZHONGSHENG PHARMACEUTICAL CO., LTD; LONG, Chaofeng; CHEN, Zhengxia; CHEN, Xiaoxin; ZHANG, Yang; LIU, Zhuowei; LI, Peng; CHEN, Shuhui; LIANG, Guibai; XIE, Cheng; LI, Zhengwei; FU, Zhifei; HU, Guoping; LI, Jian; (276 pag.)EP3293177; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 172078-33-0,Some common heterocyclic compound, 172078-33-0, name is Indolin-5-ol, molecular formula is C8H9NO, 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 stirred solution of 6-(3,5-dimethylisoxazol-4-yl)-7-methoxy-2-oxo-l-(pyri- din-2-ylmethyl)-l,2-dihydroquinoline-3-carbaldehyde (intermediate- le) (0.2 g, 0.51 mmol) in titanium isopropoxide (5 mL) was added indolin-5-ol (0.1 g, 0.77 mmol) followed by stirring at RT for 16 h. After stirring, methanol (20 mL) was added to the mixture at 0 C followed by NaCNBH4 (0.16 g, 2.56 mmol). The mixture was stirred at RT for 2 h. The mixture was then quenched with ammonium hydroxide and the solids were filtered off. The filtrate was extracted with EtOAc (100 mL x 2), washed with water (100 mL) and brine (100 mL), dried over sodium sulphate and concentrated under reduced pressure. The residue was purified to get the title compound as pale brown solid (0.016 g, 6 %). 1H NMR (400 MHz, CDC13) delta 8.60 (d, J=4.8 Hz, 1H), 7.86 (s, 1H), 7.67 (t, J=7.8 Hz, 1H), 7.34 (d, J=7.8 Hz, 1H), 7.27 (s, 1H), 7.23-7.20 (m, 2H), 6.69 (s, 1H), 6.60-6.48 (m, 2H), 5.74 (s, 2H), 4.29 (s, 2H), 3.79 (s, 3H), 3.61-3.59 (m, 2H), 3.10-3.00 (m, 2H), 2.25 (s, 3H), 2.11 (s, 3H); LC-MS: m/z 509.3 (M+H)+.

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

Reference:
Patent; ORION CORPORATION; SAMAJDAR, Susanta; ABBINENI, Chandrasekhar; LINNANEN, Tero; WOHLFAHRT, Gerd; (120 pag.)WO2017/1733; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 172078-33-0, These common heterocyclic compound, 172078-33-0, name is Indolin-5-ol, 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.

Take one 100mL eggplant-shaped bottle, add 0.54g (4.00mmol) 5-hydroxyindoline, 1.36g (4.16mmol) Cs2CO3 and 30mL absolute ethanol, stir at room temperature for 1h, and 0.79g (3.97mmol) 3a- 1 or 3a-2 and 0.10g (0.60mmol) KI were put into the reaction solution, and the reaction was refluxed at 80 for more than 4h. The progress of the reaction was monitored by thin layer chromatography until the 5-hydroxyindoline point completely disappeared, and vacuum distillation The solvent was removed, and the residue was a pale yellow solid. The residue was dissolved with 30 mL each of water and ethyl acetate. The liquid was separated. The aqueous phase was extracted twice with ethyl acetate, 15 mL each time. The organic phases were combined, washed with water, and washed with saturated brine. Dry over anhydrous sodium sulfate, filter to remove sodium sulfate, the filtrate was distilled under reduced pressure to remove the solvent, the residue was sampled with 100-200 mesh silica gel, and separated by column chromatography (PE:EA=12:1 elution) to give a light yellow oil 4-((Indoline-5-)oxymethyl) benzaldehyde (4d-3, 0.72g, yield 71.29%) or 3-((Indoline-5-)oxymethyl) benzaldehyde (4d-4, 0.77g, yield 76.24%).

The synthetic route of 172078-33-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The Chinese People’s Liberation Army Military Academy Of Sciences Military Medical Institute; Wang Liyun; Tong Kun; Shi Weiguo; Cheng Jingchao; Yu Zixing; Ren Fengxia; Zhou Hu; Xiong Ying; (49 pag.)CN111217776; (2020); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 172078-33-0 as follows. Formula: C8H9NO

Take one 100mL eggplant-shaped bottle, add 0.54g (4.00mmol) 5-hydroxyindoline, 1.36g (4.16mmol) Cs2CO3 and 30mL absolute ethanol, stir at room temperature for 1h, and 0.79g (3.97mmol) 3a- 1 or 3a-2 and 0.10g (0.60mmol) KI were put into the reaction solution, and the reaction was refluxed at 80 for more than 4h. The progress of the reaction was monitored by thin layer chromatography until the 5-hydroxyindoline point completely disappeared, and vacuum distillation The solvent was removed, and the residue was a pale yellow solid. The residue was dissolved with 30 mL each of water and ethyl acetate. The liquid was separated. The aqueous phase was extracted twice with ethyl acetate, 15 mL each time. The organic phases were combined, washed with water, and washed with saturated brine. Dry over anhydrous sodium sulfate, filter to remove sodium sulfate, the filtrate was distilled under reduced pressure to remove the solvent, the residue was sampled with 100-200 mesh silica gel, and separated by column chromatography (PE:EA=12:1 elution) to give a light yellow oil 4-((Indoline-5-)oxymethyl) benzaldehyde (4d-3, 0.72g, yield 71.29%) or 3-((Indoline-5-)oxymethyl) benzaldehyde (4d-4, 0.77g, yield 76.24%).

According to the analysis of related databases, 172078-33-0, the application of this compound in the production field has become more and more popular.

Reference of 172078-33-0, 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. 172078-33-0, name is Indolin-5-ol belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 49: 5-Hydroxy-2,3-dihydro-indole-l-carboxylic acid tert-butyl esterA mixture of 2,3-dihydro-lH-indol-5-ol (1.0 g, 7.8 mmol), di-te/t-butyldicarbonate (4.0 g, 18 mmol), chloroform (20 mL) and saturated sodium bicarbonate aq. (8 mL) was stirred at room temperature over night. The organic phase was separated and washed twice with water, dried over MgSO4, filtered and concentrated to give crude product. The crude material was treated with ether and filtered to give product (1.1 g, yield: 60%). ESI-MS: 258.10 (M+23)+, 1H NMR (400 MHz, DMSO) delta 9.00 (s, IH), 7.48 (ws, IH), 6.61 (d, IH), 6.51 (dd, IH), 3.84 (t, 2H), 2.96 (t, 2H), 1.48 (s, 9H).

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

Reference:
Patent; BIOGEN IDEC MA INC.; THOMAS, Jermaine; LIU, Xiaogao; LIN, Edward, Yin-Shiang; ZHENG, Guo, Zhu; MA, Bin; CALDWELL, Richard, D.; GUCKIAN, Kevin, M.; KUMARAVEL, Gnanasambandam; TAVERAS, Arthur, G.; WO2011/17561; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 172078-33-0, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 172078-33-0 as follows.

Compound 2-2: To a solution of 1-chloroisoquinoline-5-sulfonylchloride (0.4 g, 1.53 mmol) in DCM (10 mL) was added TEA (318 muL, 2.29 mmol) and indolin-5-ol (226.9 mg, 1.68 mmol). The mixture was stirred at 25 C. for 12 h under an N2 atmosphere. The reaction mixture was filtered and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography (SiO2, petroleum ether:ethyl acetate=10:1 to 1:1). Compound 2-2, 1-[(1-chloro-5-isoquinolyl) sulfonyl]indolin-5-ol (350 mg, 970.0 mumol, 63.6% yield), was obtained as a yellow solid.

According to the analysis of related databases, 172078-33-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Cervello Therapeutics LLC; Lee, Matthew Randolph; Varano, JR., Anthony Joseph; (53 pag.)US2020/140412; (2020); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 172078-33-0, name is Indolin-5-ol, 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. COA of Formula: C8H9NO

Example 48 1-(6,7-Dimethoxy-quinazolin-4-yl)-2,3-dihydro-1H-indol-5-ol methanesulfonate salt Utilizing a procedure analogous to that described in Example 1 (with conversion to the methanesulfonate salt analogous to that described in Example 44), this product was prepared in 90% yield from 5-hydroxy-indoline (1.1 eq.), and 4-chloro-6,7-dimethoxy-quinazoline (1.0 eq) in i-PrOH. (M.P. 245-250 C. (dec); LC-MS: 324 (MH+); anal. RP18-HPLC RT: 2.76 min.).

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

Reference:
Patent; Pfizer Inc.; US5736534; (1998); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem