Month: October 2020

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.55052-28-3,4-Chloro-7-azaindole,as a common compound, the synthetic route is as follows.

1H-4-chloro-pyrrolo[2,3-b]pyridine (0.765 g, 5 mmol, 1 eq.) was dissolved in DMF (7.5 mL, 1 .5 mL / mmol SM). NBS (0.935 g, 5.25 mmol) was added and the resulting solution was stirred at ambient temperature overnight, protected from light. Then, the solution was poured into ice-cold water (25 mL, 5 mL / mmol SM) and cooled into an ice bath. After ~10min the remaining suspension was filtered and the solid washed four times with 10 mL ice-cold water. Then the solid was collected and dried under high vacuum to give FH5295 as a yellow solid (1 .12 g, 4.8 mmol) in 96 % yield. 1H NMR (300 MHz, DMSO-d6) delta: 7.23 (d, J = 5.1 Hz, 1 H, H-5), 7.81 (d, J = 2.7 Hz, 1 H, H-2), 8.21 (d, J = 5.1 Hz, 1 H, H-6), 12.44 (br s, 1 H, N-H). 13C NMR (75 MHz, DMSO-d6) delta: 85.03 (C-3), 1 14.58 (C-3a), 1 17.13 (C-5), 127.71 (C-2), 134.17 (C-4), 144.18 (C-6), 147.98 (C-7a). HRMS (ESI): calculated for C7H5BrCIN2 ([M+H]+): 230.9319, found: 230.9332. Melting point: 210 C (decomposed)., 55052-28-3

55052-28-3 4-Chloro-7-azaindole 11389493, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Patent; UNIVERSITEIT GENT; UNIVERSITEIT ANTWERPEN; HULPIA, Fabian; VAN CALENBERGH, Serge; CALJON, Guy; MAES, Louis; (146 pag.)WO2019/76633; (2019); 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

90271-86-6,90271-86-6, 5-Bromo-3-cyanoindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of ie/ -butyl 4-(4-(4,4,5,5-tetramethyl- l,3,2-dioxaborolan-2- yl)benzoyl)piperazine- l-carboxylate ( 0.2 M in 1,4-dioxane, 100 mu, 0.02 mmol), was added 5-bromo-lH-indole-3-carbonitrile(0.2 M in 1,4-dioxane, 100 mu, 0.02 mmol) and potassium phosphate solution (1 M aqueous, 100 mu, 0.1 mmol). The mixture was bubbled with nitrogen and tetrakis(triphenylphosphine)palladium (0) (0.02 M in toluene, 50 mu, 1 muiotaetaomicron) was added. The resulting mixture was put on a shaker in a glove box under nitrogen atmosphere and heated at 80 C overnight. After being cooled to rt, the mixture was diluted with 0.35 mL of brine and 0.5 mL of ethyl acetate. The organic layer was separated and the aqueous layer was extracted again with ethyl acetate (0.6 mL). The combined organic layers were concentrated and the residue was dissolved in 200 mu^ of methanol. HC1 solution (50 mu^ , 4 N in 1,4-dioxane, 0.2 mmol) was added. The mixture was put on a shaker at 50 C for 1 hour. The reaction mixture was concentrated in vacuo and the residue was dissolved in a solution of 10% N,N-diisopropylethylamine in dimethylacetamide (200 mu). 1-Hydroxycyclopropanecarboxylic acid (0.2 M in 1,4- dioxane, 120 mu, 0.024 mmol) was added, followed by BOP solution (0.5 M in 1,2- dichloroethane, 48 mu^ , 0.024 mmol). The mixture was put on a shaker at rt for 2 hour. The reaction mixture was then diluted with 0.45 mL of IN NaOH in brine and 0.5 mL of ethyl acetate. The organic layer was separated and the aqueous layer was extracted again with ethyl acetate (0.6 mL). The combined organic layers were concentrated and the residue was purified by HPLC: Water Autopurification MS -directed HPLC prep fraction collection with the following conditions Column, Waters XBridge OBD CI 8, 5muiotaeta, 19x50mm; flow rate 20ml/min; mobile phase, water with 0.1% ammonium hydroxide (A) and methanol with 0.1% ammonium hydroxide(B) running the following gradient 0 to 2mins (15%B), 2 to 6 mins (15-100%B); Detector ZQ Mass Detector in electrospray ionization mode. 5-(4-(4-(l-Hydroxycyclopropanecarbonyl)piperazine-l- carbonyl)phenyl)-lH-indole-3-carbonitrile (3.5 mg, 8.4 muiotaetaomicron, 42% yield) was obtained. MS (ESI, pos. ion) m/z: 415 (M + 1).

The synthetic route of 90271-86-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; FORMA THERAPEUTICS, INC.; BAIR, Kenneth, W.; LANCIA, David, R.; LI, Hongbin; LOCH, James; LU, Wei; MARTIN, Matthew, W.; MILLAN, David, S.; SCHILLER, Shawn, E.r.; TEBBE, Mark, J.; WO2014/164749; (2014); 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.81868-12-4,2-(5-Bromo-1H-indol-3-yl)ethanamine hydrochloride,as a common compound, the synthetic route is as follows.

81868-12-4, A stirred suspension of 5-bromotryptamine hydrochloride (17.0 g, 61.7 mmol) in 250 mL of 0.1 N aqueous sulfuric acid was treated with isovaleraldehyde (10.0 mL, 92.6 mmol). The suspension was heated at 80 C. for 3 hr. The resulting solution was allowed to cool to ambient temperature then further cooled to 0 C. in an ice-water bath. The precipitated product was filtered, washed with MTBE (300 mL), dried overnight under high vacuum to give 6-bromo-1-isobutyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole hydrochloride 19.3 g (92%) as a white solid. 1H NMR (600 MHz, DMSO-d6) delta 11.41 (s, 1H), 9.92 (br. s., 1H), 9.46 (br. s., 1H), 7.66 (d, J=1.88 Hz, 1H), 7.33 (d, J=8.56 Hz, 1H), 7.21 (dd, J=1.88, 8.56 Hz, 1H), 4.66 (br. s., 1H), 3.54 (d, J=12.14 Hz, 1H), 3.27 (br. s., 1H), 2.86-3.01 (m, 2H), 2.01-2.09 (m, 1H), 1.91-1.99 (m, 1H), 1.83 (ddd, J=4.09, 10.23, 14.28 Hz, 1H), 1.03 (d, J=6.31 Hz, 3H), 0.97 (d, J=6.59 Hz, 3H).

81868-12-4 2-(5-Bromo-1H-indol-3-yl)ethanamine hydrochloride 13241175, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Patent; ALCON RESEARCH, LTD.; Ellis, David Archer; Mohapatra, Suchismita; Namil, Abdelmoula; Chen, Hwang-Hsing; Severns, Byron; Belanger, David B.; US2013/116219; (2013); 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.3189-22-8,7-Methoxyindole,as a common compound, the synthetic route is as follows.

7-methoxyindole (0.2 mmol) was added to a 4 mL reaction flask.1,2-diphenyldisulfide (0.3 mmol),Potassium tert-butoxide (0.4 mmol) and DMF (2.0 mL) were stirred at room temperature. TLC tracks the detection reaction. After 2 hours, the starting material was completely converted.Water and dichloromethane were added to the reaction system, and the organic layer was separated.Wash the water layer twice with dichloromethane, combine all the organic layers, andWash twice with water. The organic layer was dried over anhydrous sodium sulfate, concentrated, and then purified by column chromatography (To the product 32 mg, the yield was 63percent, and the reaction process was as follows:, 3189-22-8

3189-22-8 7-Methoxyindole 76660, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Patent; Wenzhou Medical University; Song Zengqiang; Zhan Lingling; Qian Jianchang; Liang Guang; Liu Zhiguo; (14 pag.)CN108586311; (2018); 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.1953-54-4,5-Hydroxyindole,as a common compound, the synthetic route is as follows.

A mixture ofof5-hydroxyindole 1 (750 mg, 5.63 mmol), benzyl bromide (1.05 g, 6.19 mmol), K2C03 (2.30 g, 16.89 mmol) and DMF (10 mL), was stirred at RT for 16 h. The mixture was partitioned between water (100 mL) and EtOAc (50 mL). The organic layer was separated and the aq. layer re-extracted with additional EtOAc (50 mL). The combined organic layers were dried over Na2SO4, filtered, and the filtrate concentrated under reduced pressure. The residue was purified (silica gel; eluting with 0-100% EtOAc in hexanes), to afford compound 2 (1.12 g, 88%) as a light yellow solid. LCMS Mass: 224.0 (M+1)., 1953-54-4

As the paragraph descriping shows that 1953-54-4 is playing an increasingly important role.

Reference£º
Patent; PHARMAKEA, INC.; ROWBOTTOM, Martin, W.; HUTCHINSON, John, Howard; (185 pag.)WO2017/3862; (2017); 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

6052-68-2, 2,3,4,9-Tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

6052-68-2, Example 10; General procedure for the preparation of 1,2,3,4-tetrahydro-beta-carboline-3-carboxylates; 1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid 9a (50mmol), methanol or ethanol (250ml) and thionyl chloride (10ml) were added into a 500 ml round-bottom flask. The mixture was refluxed for 1 to 2 h. After alcohol was evaporated in reduced pressure, 100ml cold water was added. The pH was adjusted to 9 with saturated NaHCO3 solution. Then the mixture was extracted with ethyl acetate. The organic phases were combined, washed with water and brine, dried over anhydrous sodium sulfate, filtered, concentrated in vacuum. Recrystallization was conducted with ethyl acetate. Examples 11 and 12 were treated according to the above procedures.; Example 11; Synthesis of methyl 1,2,3,4-tetrahydro-beta-carboline-3-carboxylate (9b): white solids were obtained, and the yield was 57%.

The synthetic route of 6052-68-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Xinjiang Huashidan Pharmaceutical Research Co., Ltd.; EP1634881; (2006); 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

1000340-39-5, 3-Bromo-4-chloro-7-azaindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a suspension of sodium hydride (0.22 g,5.19 mmol) in N,N-dimethylformamide (15 mL) was added 3-bromo-4-chloro-1H-pyrrolo[2,3-b]pyridine (1.0 g,4.32 mmol) at 0 C. and the suspension was stirred at ambient temperature for 0.5 hours. The mixture was cooled to 0 C. and (2-chloromethoxyethyl)trimethylsilane (0.92 mL,5.19 mmol) was added. The reaction mixture was allowed to warm to ambient temperature and stir for 1 hour. The reaction mixture was quenched with ice and extracted with ethyl acetate. The organic layer was washed with water,brine,dried over anhydrous sodium sulfate,filtered and concentrated in vacuo. The crude material was purified using flash chromatography (5% ethyl acetate/hexane) to provide 3-bromo-4-chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine as a viscous oil (1.5 g,95% yield): MS (ES) m/z 362.0 (M+H)., 1000340-39-5

As the paragraph descriping shows that 1000340-39-5 is playing an increasingly important role.

Reference£º
Patent; ACLARIS THERAPEUTICS, INC.; JACOBSEN, Eric Jon; ANDERSON, David Randolph; BLINN, James Robert; HOCKERMAN, Susan Landis; HEIER, Richard; MUKHERJEE, Paramita; (196 pag.)US2020/48262; (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.1196-70-9,1H-Indole-6-carbaldehyde,as a common compound, the synthetic route is as follows.

1196-70-9, Step 3. Synthesis of (E)-N?-(( 1 H-indol-6-yl)methylene)-2-(2-(furan-3 -yl)-6- methylphenoxy)acetohydrazide: 2-(2-(furan-3 -yl)-6-methylphenoxy)acetohydrazide (70 mg,0.28 mmol) and 1H-indol-6-carbaldehyde (45 mg, 0.31 mmol) were dissolved in EtOH 2 mL, followed by stirring at 100 C for 12 hours. After the completion of the reaction, the reaction mixture was added with water, and extracted with ethyl acetate. The obtained organic layer was dried over magnesium sulfate, and purified by column chromatography (ethyl acetate:hexane = 1:1) to obtain Compound 313 (20 mg, 19%).?H NMR (400 MHz, DMSO-d6): 6 11.41 (m, 2H), 8.45-8.01 (2s, IH), 8.30 (m, IH), 7.72 (m,1H), 7.46 (m, 4H), 7.10 (m, 4H), 6.44 (m, 1H), 4.70 (s, 1H), 4.25 (s, 1H), 2.30 (m, 3H).

1196-70-9 1H-Indole-6-carbaldehyde 2773435, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Patent; CHONG KUN DANG PHARMACEUTICAL CORP.; INJE UNIVERSITY INDUSTRY-ACADEMIC COOPERATION FOUNDATION; CHOI, HoJin; LEE, JaeWon; LEE, ChangGon; HA, NiNa; SEO, Su Kil; LEE, SunMi; LEE, Song-Min; WO2014/35149; (2014); 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.107516-75-6,Diethyl 1H-indole-2,6-dicarboxylate,as a common compound, the synthetic route is as follows.

Step 5: Synthesis of diethyl l-{(2S)-4-[(tert-butoxycarbonyl)amino]butan-2-yl}-1H- indole-2,6-dicarboxylateTo a suspension of hexane washed 60% sodium hydride in mineral oil (91 mg, 2.3 mmol) in DMF (2.5 mL) under nitrogen atmosphere to 0 C is added a solution of diethyl 1H- indole-2,6-dicarboxylate (619 mg, 2.4 mmol) in DMF (4 mL). The mixture is stirred for 20 min at 0 C and a solution of tert-butyl (6R)-6-methyl-1,2,3-oxathiazinane-3- carboxylate 2,2-dioxide (518 mg, 2.1 mmol) in DMF (2.5 mL) is added. The reaction mixture is stirred for 30 min at 0 C and is warmed to room temperature and stirred for 72 h. Water and NH4C1 solution are added and the mixture is stirred for 15 min. The aqueous mixture is extracted with EtOAc (50 mL) and the organic layer is washed with water, brine, dried (MgS04) and concentrated to afford the title crude compound (1.1 g) which is used in the next step without purification.

107516-75-6, As the paragraph descriping shows that 107516-75-6 is playing an increasingly important role.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOYER, Stephen, James; GAO, Donghong, Amy; GUO, Xin; KIRRANE, Thomas, Martin, Jr.; SARKO, Christopher, Ronald; SNOW, Roger, John; SOLEYMANZADEH, Fariba; ZHANG, Yunlong; WO2011/71716; (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

52415-29-9, 6-Bromoindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

52415-29-9, (a) 6-Bromo-1-methylindole STR25 Sodium hydride (4.10 g of a 60% dispersion in paraffin wax) was added to a stirred solution of 6-bromoindole (10 g, 51.3 mmol) in tetrahydrofuran (10 ml) at 0 C. under a nitrogen atmosphere. After 1 hour iodomethane (6.38 ml, 102.6 mmol) was added and the cooling bath removed. After 12 hours methanol was added dropwise until effervescence ceased and then the solvent was removed in vacuo. The thick residue was diluted with dichloromethane and washed first with water then with brine. The organic layer was dried (magnesium sulphate) and concentrated in vacuo to give a dark yellow oil. Filtration through a plug of silica with 90% hexane/10% ethyl acetate as eluant gave the subtitle compound as a pale yellow oil (10.5 g). 1 H NMR (300 MHz, CDCl3): delta=3.75 (d, 3 H), 6.40 (d, 1 H), 7.00 (d, 1 H), 7.20 (d, 1 H), 7.50 (d, 1 H), 7.45 (s, 1 H). LRMS (Thermospray): 209.7 (MH+)

As the paragraph descriping shows that 52415-29-9 is playing an increasingly important role.

Reference£º
Patent; Pfizer Inc.; US6017945; (2000); 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