Tag: M.W:200-300

348-36-7, Ethyl 5-fluoro-1H-indole-2-carboxylate is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

a) To a solution of 5-fluoroindol-2-ethyl ester (200 mg, 0.965 mmol) in dimethylsulfoxide (6 mL) is added potassium tert-butylate (108 mg, 0.965 mmol) and the mixture is stirred at 50¡ã C. for 30 minutes. After cooling to room temperature bromoethane (0.081 mL, 1.06 mmol) is added and the mixture is stirred at room temperature for 2.5 hours. With cooling water is added and the mixture is extracted with ethyl acetate. The organic layer is washed with water and saturated aqueous NaCl solution, dried over MgSO4 and the solvent is evaporated in vacuo to yield 200 mg of 1-ethyl-5-fluoro-1H-indole-2-carboxylic acid ethyl ether (ESI mass spectrum: [M+H]+=236).

348-36-7, As the paragraph descriping shows that 348-36-7 is playing an increasingly important role.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; Anderskewitz, Ralf; Martyres, Domnic; Oost, Thorsten; Rist, Wolfgang; Seither, Peter; US2013/23576; (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.166104-20-7,1-Boc-5-Aminoindole,as a common compound, the synthetic route is as follows.

To a stirred solution of tert-butyl 5-amino-1H-indole-1-carboxylate (1, 5.0 g, 21.55 mmol) in acetonitrile (50 mL) at 0 C., N-bromosuccinimide (4.23 g, 23.70 mmol) was added portion-wise. The mixture was stirred at same temperature for 3 h. Next, the reaction was poured into ice-cold water and extracted with ethyl acetate. The organic layer was washed with brine solution, dried over anhydrous sodium sulfate, filtered, and concentrated to dryness under reduced pressure. The crude product was purified by Combiflash (40 g, RediSep column) using 0-30% ethyl acetate in hexanes as eluent. The desired fractions were concentrated under reduced pressure to afford tert-butyl 5-amino-4-bromo-1H-indole-1-carboxylate (2) as a brown liquid. Yield: 5.8 g, 86%; MS (ESI) m/z 311.08 [M+1]+., 166104-20-7

166104-20-7 1-Boc-5-Aminoindole 11593831, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Patent; eFFECTOR Therapeutics, Inc.; ERNST, Justin T.; REICH, Siegfried H.; SPRENGELER, Paul A.; XIANG, Alan X.; (41 pag.)US2019/119256; (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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.15903-94-3,6-(Benzyloxy)-1H-indole,as a common compound, the synthetic route is as follows.

To a stirred, cooled [(10OC)] suspension of sodium hydride (80.7 g of a 60% dispersion in mineral oil, 2.02 mol) in anhydrous THF (1.9 L) was added a solution of 6- benzyloxyindole (375 g, 1.68 mol) in anhydrous THF (1.9 L) keeping the temperature below [25OC.] After 2 h at 10C, propylene oxide (140 mL, 2.0 mol) was added dropwise keeping the temperature below [25OC.] After 48 h at 10C, propylene oxide (71 mL, 1.0 mol) was added. After 96 h at 10 oC, saturated aqueous potassium dihydrogenphosphate (3.8 L) and ethyl acetate (3.8 L) were carefully added, the layers were separated and the aqueous solution was extracted with 3.8 L of ethyl acetate. The combined organic extracts were dried over sodium sulfate and concentrated in vacuo to yield a solid (520 g, 110%, contains mineral oil).

15903-94-3, 15903-94-3 6-(Benzyloxy)-1H-indole 260804, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Patent; ALCON, INC.; WO2003/101379; (2003); 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

91348-45-7, Ethyl 3-bromo-1H-indole-2-carboxylate is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,91348-45-7

General procedure: To a mechanically stirred mixture of (1) (27.97 mmol),K2CO3 (83.91 mmol) and dry DMF (50 mL), benzyl bromideor 4-chlorobenzyl bromide (30.77 mmol) was addeddropwise respectively. After stirring for 48 h, the solutionwas filtered and the filtrate was extracted with ethyl acetate(3 ¡Á 20 mL). The combined organic extracts were washedwith water (50 mL) and brine (50 mL), dried over sodiumsulfate and concentrated. The crude product was purified bycolumn chromatography using a mixture of ethyl acetate/hexane (20:80) as eluent to give the title compounds (2a/b).

91348-45-7 Ethyl 3-bromo-1H-indole-2-carboxylate 4715017, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Article; Kaur, Jeewanjot; Singh, Amanjot; Singh, Gagandeep; Verma, Raman K.; Mall, Rajiv; Medicinal Chemistry Research; vol. 27; 3; (2018); p. 903 – 914;,
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.1211594-25-0,4-Bromo-1H-indole-7-carboxylic acid,as a common compound, the synthetic route is as follows.

3. 4-Bromo- 1 H-indole-7-carboxamide; A mixture of 4-bromo-1H-indole-7-carboxylic acid (10.04 g, 75% purity, 31.2 mmol), EDC (8.96 g, 46.7 mmol), and 1-hydroxybenzotriazole hydrate (7.16 g, 46.7 mmol) in THF (198 mL) and CH2CI2 (247 mL) was stirred at room temperature for 1 h. The mixture was then bubbled with NH3 gas for 15 min and stirred at room temperature for 4 h. LCMS showed residual starting material, so aqueous ammonium hydroxide (4.85 mL, 125 mmol) was added and the mixture was stirred at room temperature overnight. After 20 h, the mixture was concentrated and partitioned between NaHCO3 (aq) and EtOAc. The organic phase was washed with brine, dried and concentrated. The residue was suspended in EtOAc and the solid was collected by filtration and air-dried to provide the desired product. The filtrates were subjected to column chromatography on silica gel (40g), eluting with EtOAc -hexane (gradient from 20:80 to 50:50) to provide additional desired product for a total of 4.86 g (65% yield) over two steps. LCMS (M-H)-: 237.2, 239.2.

1211594-25-0, As the paragraph descriping shows that 1211594-25-0 is playing an increasingly important role.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; LIU, Chunjian; LIN, James; DELUCCA, George V.; BATT, Douglas G.; LIU, Qingjie; WO2011/159857; (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

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

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

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

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

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