Tag: M.W:100-200

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.31241-19-7,5-Methoxy-2,3,3-trimethyl-3H-indole,as a common compound, the synthetic route is as follows.

EXAMPLE II Under an inert hydrogen or argon atmosphere 1.4 ml of 1M solution of BBr3 in dichloro-methane is added to a solution of 1.2 10-3 mole of 5-methoxy 2,3,3-trimethyl indolenine in 1.5 ml dichloromethane at 0 C. under stirring so as to obtain 5-hydroxy 2,3,3-trimethyl-indolenine.

31241-19-7, The synthetic route of 31241-19-7 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Essilor International (Compagnie Generale d’Optique; US5114621; (1992); A;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

7506-66-3,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.7506-66-3,cis-Hexahydro-1H-isoindole-1,3(2H)-dione,as a common compound, the synthetic route is as follows.

Cis-8-azabicyclo[4,3,0]nonane To a slurry of lithium aluminium hydride (17.1 g) in dry diethyl ether (375 ml) under a nitrogen atmosphere, cis-hexahydrophthalimide (23.0 g) in dry tetrahydrofuran (300 ml) was added over a two-hour period. The mixture was refluxed for 2.5 hours, cooled and treated very slowly with excess of water. The precipitate was filtered off and the filtrate was evaporated to yield the title compound as a viscous oil, which was used in the next step without purification.

The synthetic route of 7506-66-3 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Leo Pharmaceutical Products Ltd. A/S; US4181659; (1980); A;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.343-90-8,1-(5-Fluoro-1H-indol-3-yl)-N,N-dimethylmethanamine,as a common compound, the synthetic route is as follows.

A. 5-Fluoroindole-3-acetonitrile A mixture of 38 g of 3-dimethylaminomethyl-5-fluoroindole (0.198 mole; cf. Hoffman et al. J. Heterocyclic Chem. 2, 298 (1965); of the 5-fluorogramine therein) in 500 ml of methanol was prepared. Then a solution of 25.7 g of KCN (0.396 mole) in 50 ml of water was added, with stirring. The stirred mixture was cooled to 20 C. and 34.6 ml of methyl iodide (0.556 mole) was added over a 20 minute period. The mixture was then stirred at about 20 C. for 16 hours. The solvent was removed by evaporation and the residue was partitioned between ether and water. The ether portion was washed with water, 5% HCl, saturated NaHCO3 solution, water, and brine, dried over MgSO4 and evaporated to leave a liquid residue. This residue was distilled at reduced pressure in a Kugelrohr apparatus. The fraction distilling at 134-140 C. and 0.3 to 0.1 Torr was collected and crystallized from ethyl acetate-petroleum ether, mp 58-59, yield 5.3 g (44%).

343-90-8, The synthetic route of 343-90-8 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Miles Laboratories, Inc.; US4283336; (1981); A;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

6127-17-9, 6-Chloro-2-methyl-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

6127-17-9, Example 6Synthesis of CBX0044-(2-(6-chloro-2-methyl-lH-indol-l-yl)ethyl)morpholine[0161] To a solution of 2-chloroethylmorpholine HC1 (134 mg, 0.72 mmol) in 0.3 mL DMSO was added pulverized KOH (102 mg, 1.81 mmol), then after 10 min, a solution of 6- chloro-2-methylindole (100 mg, 0.60 mmol) in 0.2 mL DMSO was added and the reaction stirred at room temperature overnight. Additional 2-chloroethylmorpholine (22 mg, 0.12 mmol) and KOH (17 mg, 0.3 mmol) added and stirred overnight. The reaction mixture was partitioned between ?0 and toluene, and the organic extract washed two times with ?0, dried over MgS04, filtered, and concentrated in vacuo. The crude product was purified via silica gel chromatography using a gradient from 0 to 50% ethyl acetate in hexane to give a final yield of 149 mg (0.54 mmol). XH NMR (500 MHz, CDC13, delta): 2.44 (s, 3H), 2.49 (t, J = 4.4 Hz, 4H), 2.62 (t, J = 7.2 Hz, 2H), 3.73 (t, J = 4.5 Hz, 4H), 4.11 (t, J= 7.2 Hz, 2H), 6.23 (s, 1H), 7.06 (dd, J = 8.4 Hz, 1.7 Hz, 1H), 7.28 (s, 1H), 7.42 (d, J = 8.3 Hz, 1H). 13C NMR (500 MHz, CDC13, delta): 12.79, 41.18, 54.11, 57.83, 67.5, 100.30, 108.95, 119.90, 120.53, 126.40, 126.70, 137.06, 137.37. MS m/z 279.3 [M + H]+.

The synthetic route of 6127-17-9 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; UNIVERSITY OF WASHINGTON THROUGH ITS CENTER FOR COMMERCIALIZATION; STELLA, Nephi; KLINE, Toni; WO2012/24670; (2012); A2;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

640735-23-5, 4-Fluoro-7-azaindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

640735-23-5, To a solution of 4-fluoro-1H-pyrrolo[2,3-b]pyridine (4.07 g, 29.9 mmol) in N,N- dimethylformamide (250 mL) was added N-bromosuccinimide (6.20 g, 34.8 mmol) in portions at 0 C. The reaction mixture was stirred at 0 C for 1 h. The reaction was quenched with water (200 mL) and the precipitate was collected to afford the title compound (4.06 g, 18.9 mmol, 63%) as an off-white solid.LCMS Method A: 99%, tR 1.328 min, m/z = 215.0 [M+H]+

As the paragraph descriping shows that 640735-23-5 is playing an increasingly important role.

Reference：
Patent; BIOBLOCKS, INC.; VISIONARY PHARMACEUTICALS; MEYER, Stephen Todd; WADE, Warren Stanfield; ZAPF, James W.; GERENCSER, Janos; GYIMOTHY, Balazs; (282 pag.)WO2020/23393; (2020); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.935269-27-5,3-Oxoisoindoline-4-carboxylic acid,as a common compound, the synthetic route is as follows.

935269-27-5, To a stirred solution of 4a-d, f-j (1.0 eq) in DMF was added HOBt (2.0 eq), HBTU (2.0 eq), and DIPEA (3.0 eq) followed by 3-oxo-2,3-dihydro-lH-isoindole-4-carboxylic acid (1.0 eq) and allowed to stir at rt for 12 h. The reaction mixture was then diluted with water. The product was filtered, washed with water, dried under vacuum, and obtained in 62-71percent yield. This product was then treated with 2 MHO in Et^O to remove the Boc group giving the Oxoisoindoline-Orn- benzimidazole intermediate. The solvent was then evaporated to dryness and the crude material was dried in vacuo. To a stirred solution of the corresponding Oxoisoindoline-Orn-benzimidazole intermediate in dry MeOH was added TEA (4.0 eq) followed by ethyl haloacetimidate HCl (2.0 eq). The reaction was stirred under N2 at rt for 3 h. Solvents were then evaporated under reduced pressure and the crude product was purified by reverse phase HPLC using MeCN:H20 (0.5percent TFA) as an eluent to give compounds 7a-v in 41-57percent yield.

As the paragraph descriping shows that 935269-27-5 is playing an increasingly important role.

Reference：
Patent; UNIVERSITY OF MASSACHUSETTS; THOMPSON, Paul, R.; MUTH, Aaron; SUBRAMANIAN, Venkataraman; (129 pag.)WO2018/102262; (2018); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

399-51-9, 6-Fluoro-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Synthesis of the Compound of Formula IIDetailed syntheses of the compound of Formula II from commercially available 6-fluoroindole are provided below. Scheme II uses diethoxymethane and dimethylamine to generate the ?iminium ion species?. An alternative procedure using formaldehyde in place of diethoxymethane is also provided below. Synthetic Procedure:Preparation of formaldehyde was carried out in reactor A. The synthesis of the compound of Formula II was carried out in reactor B. Precipitation of the final product was carried out in reactor C.Procedure:To reactor A were charged diethoxymethane (65 ml/54 g), water (50 ml) and formic acid (39 ml/47 g). The mixture was heated to about 80 C./reflux for about 2 hours and then cooled to about 20 C. To reactor B were charged 6-fluoroindole (50 g) and 80% acetic acid (66 ml/70 g, 2.5 eq. to 6-fluoroindole). The suspension was cooled to 2-5 C. 40% Dimethylamine (aq) (103 ml/92 g, 2.2 eq. to 6-fluoroindole) was added drop-wise to reactor B keeping the temperature below about 15 C. The reaction mixture was stirred for about 20 minutes and at the same time the temperature was adjusted to 2-4 C.The mixture from reactor A (DEM, water, formic acid, formaldehyde and ethanol at about 20 C.) was added drop-wise to reactor B while keeping the temperature at 2-8 C. The reaction mixture was stirred for additional 10 minutes at 2-8 C. The reaction mixture was slowly warmed to about 40 C. over a 1 hour period. The reaction mixture was stirred at about 40 C. for an additional 1 hour. The reaction mixture was cooled to about 20 C.To reactor C was charged 3M NaOH (800 ml, 1.24 eq. to the acetic acid+the formic acid) and the solution was cooled to about 10 C. The reaction mixture from reactor B was added drop-wise to the NaOH solution in reactor C while keeping the temperature at 10-15 C. (pH>14). The suspension was stirred for 40 minutes at 5-20 C. (pH>14). The product was collected by filtration and the filter-cake was washed twice with water (2×250 ml). The product was dried at about 60 C. under vacuum for 16 hours. Yield: 95%. Purity by HPLC (280 nm): 98 area %., 399-51-9

399-51-9 6-Fluoro-1H-indole 351278, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; H. LUNDBECK A/S; US2011/152539; (2011); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

885518-25-2, 6-Fluoro-1H-indol-4-amine is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,885518-25-2

To a solution of intermediate 12 (233.00 mg, 0.61 mmol), intermediate 34c (100.00 mg,0.67 mmol), Pd(OAc)2 (137.00 mg, 0.061 mmol) and Cs2CO3 (592.00 mg, 1.82 mmol) in1,4-dioxane (5 mL) was added BNAP (38.00 mg, 0.06 1 mmol) and the reaction mixturewas heated for 3 h at 95 C. The reaction mixture was then diluted with ethyl acetate and washed with water and brine. The organic layer was dried with sodium sulfate and concentrated in vacuo to give 397 mg of intermediate 35c (quant. yield, 76% purity based on LC/MS, dark black foam) which was used in the next step without any further purification.

The synthetic route of 885518-25-2 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; JANSSEN PHARMACEUTICA NV; STANSFIELD, Ian; QUEROLLE, Olivier, Alexis, Georges; LIGNY, Yannick, Aime, Eddy; GROSS, Gerhard, Max; JACOBY, Edgar; MEERPOEL, Lieven; GREEN, Simon, Richard; HYND, George; KULAGOWSKI, Janusz, Jozef; MACLEOD, Calum; MANN, Samuel, Edward; (419 pag.)WO2018/2219; (2018); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.2795-41-7,6-Fluoroindole-3-carboxaldehyde,as a common compound, the synthetic route is as follows.

1.5 g 3-aldehyde-6-fluoroindole (ie intermediate I-1) was dissolved in isopropanol,Add 150 mg palladium on carbon and 3.2 g sodium borohydride,80 C reflux overnight.After TLC showed that the substrate disappeared,Filter to remove palladium carbon,After the filtrate is concentrated,Add water to quench excess sodium borohydride,Ethyl acetate extractionEach time 15ml,Extract 3 times.Organic layers merge,After drying over anhydrous sodium sulfate,Evaporated to drynessSilica gel column chromatography gave Intermediate I-2 (white solid, quantitative yield)., 2795-41-7

The synthetic route of 2795-41-7 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Hu Youhong; Geng Meiyu; Xing Weiqiang; Ding Jian; Ai Jing; (86 pag.)CN103664895; (2018); B;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.399-67-7,7-Fluoro-1H-indole-2-carboxylic acid,as a common compound, the synthetic route is as follows.

To a solution of 7-fluoroindole carboxylic acid (500 mg, 2.79 mmol, available from, for example, Matrix Scientific) in DMF (5 mL) was added potassium carbonate (771 mg, 11.2 mmol) followed by bromoethane (521 DL, 6.98 mmol). The reaction mixture was heated at 60 C for 2 h then further bromoethane (521 DL, 6.98 mmol) and potassium carbonate (771 mg, 11.2 mmol) were added. The reaction mixture was heated at 60 C for a further 2 h then concentrated under reduced pressure to give around 2 g of crude material as a beige solid.The material was suspended in a solution of THF (20 mL), water (20 mL) and MeOH (5 mL) then LiOH monohydrate (401 mg, 9.56 mmol) was added. The reaction mixture was stirred at rt for 16 h then concentrated under reduced pressure. The resulting crude product was treated with 2N HC1 (20 mL, aqueous), and the resulting beige solid filtered under reduced pressure then washed with water then further dried under reduced pressure to give the title compound as a beige solid (436 mg, 75%).LCMS (formic) MH+ = 208.0, Rt 1.03 mm

399-67-7, The synthetic route of 399-67-7 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; AMANS, Dominique; ATKINSON, Stephen, John; BARKER, Michael, David; CAMPBELL, Matthew; DIALLO, Hawa; DOUAULT, Clement; GARTON, Neil, Stuart; LIDDLE, John; RENAUX, Jessica, Fanny; SHEPPARD, Robert, John; WALKER, Ann, Louise; WELLAWAY, Christopher, Roland; WILSON, David, Matthew; (284 pag.)WO2016/185279; (2016); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles