Category: 15861-30-0

Reference of 15861-30-0, A common heterocyclic compound, 15861-30-0, name is Indoline-5-carboxylic acid, molecular formula is C9H9NO2, 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 a mixture of indoline-5-carboxylic acid (500 mg, 3.07 mmol) in DMF (3 mL) was added Pyridine (0.2 mL) at 0 C followed by acryloyl chloride (555 mg, 6.13 mmol). The reaction mixture was stirred at RT for 5 h. The mixture was then concentrated, DCM was added (20 mL), washed with 0.5N HC1 (10 mL), dried over Na2504, filted and concentrated in vacuo to afford 1- acryloylindoline-5-carboxylic acid (280 mg, 42%) as a yellow solid. [M+H] Calc?d for C12H11N03:218.1; Found: 218.1

The synthetic route of 15861-30-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KINNATE BIOPHARMA INC.; KANOUNI, Toufike; ARNOLD, Lee D.; KALDOR, Stephen W.; MURPHY, Eric A.; TYHONAS, John; (0 pag.)WO2020/6497; (2020); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 15861-30-0, These common heterocyclic compound, 15861-30-0, name is Indoline-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.

2, 3-Dihydro-1H-indole-5-carboxylic acid (12.4 mmol) was dissolved in DMF (5 mL) and 1, 2-dichloroethane (40 mL). DIPEA (12.4 mmol), 1- (3-dimethylaminopropyl)- 3-ethyl-carbodiimide hydrochloride (12.4 mmol), 1-hydroxybenzotriazole (12.4 mmol) and 2-aminothiazole (12.4 mmol) was added. Stirred at 50 C for 48h. HC1 (2M) (12.4 mmol) was added to the reaction mixture followed by water (30 mL). This gave a heavy precipitation which was removed by filtration. The solid was washed with water and 1,2-dichloroethane and dried. Yield: 56% 1H NMR (D6-DMSO) : 6.60 (s, 1H); 7.26 (d, 1H); 7.44-7. 54 (2H); 7.56 (d, 1H); 7. 86 (d, 1H); 8.45 (s, 1H) ; 11.51 (br s, 1H).

The synthetic route of 15861-30-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; H. LUNDBECK A/S; WO2005/39572; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 15861-30-0,Some common heterocyclic compound, 15861-30-0, name is Indoline-5-carboxylic acid, molecular formula is C9H9NO2, 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 50 ml. RBF was charged with indoline-5-carboxylic acid (2 g, 12.3 mmol), methanol (25 ml_, 0.5 M) and H2S04 (1 mlcat.). The reaction mixture was stirred at reflux for 8 h. The methanol was concentrated under reduced pressure and the resulting residue was extracted with dichloromethane (2 x 25 ml.) and the combined organic layer was washed with sat. NaHC03 (1 x 20 ml_). The combined organic layer was dried over anhydrous Na2S04 and concentrated under reduced pressure to afford methyl, indoline- 5-carboxylate (2.1 g , 2.78 g theoretical, 75.5%). The product was used directly in the next step without further purification.

The synthetic route of 15861-30-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; COLLABORATIVE MEDICINAL DEVELOPMENT PTY. LTD.; WARNER, John, C.; BALDINO, Carmen; MUOLLO, Lauren; ROSENFELD, Craig; (109 pag.)WO2019/106434; (2019); 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. 15861-30-0, name is Indoline-5-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 15861-30-0

To a solution of the indoline-5-carboxylic acid (100 mg, 0.613 mmol) indichloromethane (5 mL) and triethylamine (0.2 mL, 1.433 mmol, 2.3 equiv) at 0 C was addeddi-tert-butyl dicarbonate (268 mg, 1.228 mmol, 2 equiv). The mixture was stirred for 30 min atroom temperature before addition of saturated ammonium chloride. The organic layer wasseparated and dried over anhydrous sodium sulfate, filtered and dried under reduced pressure.The crude 1-(tert-butoxycarbonyl)indoline-5-carboxylic acid was used without furtherpurification.

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 15861-30-0.

Application of 15861-30-0,Some common heterocyclic compound, 15861-30-0, name is Indoline-5-carboxylic acid, molecular formula is C9H9NO2, 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 50 ml. RBF was charged with indoline-5-carboxylic acid (2 g, 12.3 mmol), methanol (25 ml_, 0.5 M) and H2S04 (1 mlcat.). The reaction mixture was stirred at reflux for 8 h. The methanol was concentrated under reduced pressure and the resulting residue was extracted with dichloromethane (2 x 25 ml.) and the combined organic layer was washed with sat. NaHC03 (1 x 20 ml_). The combined organic layer was dried over anhydrous Na2S04 and concentrated under reduced pressure to afford methyl, indoline- 5-carboxylate (2.1 g , 2.78 g theoretical, 75.5%). The product was used directly in the next step without further purification.

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

Related Products of 15861-30-0, 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 15861-30-0 as follows.

To a solution of indoline-5-carboxylic acid (1 1 .61 mg, 71 .18 gmol) in DCM (0.5 ml_) were added DIPEA (27.60 mg, 213.55 gmol) and HATU (40.60 mg, 106.77 gmol) at 25 C. The mixture was stirred at 25 C for 1 hr and then (2S)-2-amino-4-methylsulfanyl-N-(4-phenylthiazol-2-yl) butanamide (30.0 mg, 71 .1 8 gmol) was added. The reaction mixture was stirred at 25 C for 16 hr. The reaction mixture was concentrated in vacuum to give a residue. The residue was purified through reverse phase-HPLC (FA condition) and followed by prep-TLC (PE/EA=1 /1 ) to afford compound 80 as a white solid. 1 HNMR (400 MHz, MeOD) d = 7.88-7.86 (m, 2H), 7.63-7.59 (m, 2H), 7.39-7.36 (m, 3H), 7.28-7.26 (m, 1 H), 6.58-6.52 (m, 1 H), 4.89-4.86 (m, 1 H), 3.59-3.54 (m, 2H), 3.04-3.00 (m, 2H), 2.68-2.63 (m, 2H), 2.20 – 2.12 (m, 2H), 2.1 1 (s, 3H) ppm. LCMS (ESI) m/z: [M+H]+ = 453.0. Chiral HPLC: Cellucoat-MeOH+ACN(DEA)-40-5min-3mL-35T, 1 .444 min.

According to the analysis of related databases, 15861-30-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; FOGHORN THERAPEUTICS INC.; ANTHONY, Neville, John; MILLAN, David, Simon; VASWANI, Rishi, G.; SCHILLER, Shawn, E.R.; (239 pag.)WO2019/152437; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 15861-30-0, A common heterocyclic compound, 15861-30-0, name is Indoline-5-carboxylic acid, molecular formula is C9H9NO2, 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.

Reference Example 1 Synthesis of 1-carbobenzoxy-5-carboxyindoline To a mixture of water (20 ml) and diethyl ether (20 ml) were added 5-carboxyindoline (2.0 g) and sodium hydroxide (0.6 g), and then, under ice-water cooling, carbobenzoxy chloride (2.59 g) and water (10 ml) containing sodium hydroxide (2.1 g) were added to the mixture thereto alternatively. The mixture was stirred at room temperature for 2 hours. The reaction mixture was made acidic with 2N-hydrochloric acid and precipitated crystals were collected by filtration. Precipitates were washed with ether and air-dried to obtain the title compound (2.8 g). 1 H-NMR (DMSO-d6, delta): 3.10 (2H, t, J=8 Hz), 4.03 (2H, t, J=8 Hz), 5.23 (2H, s), 7.2-8.0 (8H, m). mp; 194-196 C.

The synthetic route of 15861-30-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chugai Seiyaku Kabushiki Kaisha; US5354753; (1994); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem