Month: October 2020

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.16136-52-0,4-Cyanoindole,as a common compound, the synthetic route is as follows.

EXAMPLE 88 1-Benzyl-4-cyanoindole Following a procedure and using relative proportions of starting materials similar to those described in Example 65, but using 4-cyanoindole as starting material, the title compound was obtained in a yield of 94%. Nuclear Magnetic Resonance Spectrum (CDCl3, 270 MHz), delta ppm: 5.37 (2H, singlet), 6.77 (1H, doublet, J=3.4 Hz), 7.05-7.50 (9H, multiplet).

16136-52-0, 16136-52-0 4-Cyanoindole 3817602, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Patent; Sankyo Company, Limited; US5877199; (1999); 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.6146-52-7,5-Nitroindole,as a common compound, the synthetic route is as follows.,6146-52-7

To a solution of 5 -nitro-1 H-indole (2.Og, 12.3mmol) in acetone (20ml), powdered potassium hydroxide (3.4g, 60.7mmol, 5eq) was added followed by the addition methyl iodide (2.6 Ig, 18.5mmol, 1.5eq) at O0C. The reaction mixture was heated to reflux for 10 hr. The solvent was evaporated and water was added. The compound was extracted with ethyl acetate, dried over anhydrous sodium sulphate, filtered and the organic layer was concentrated to dryness to yield l-methyl-5 -nitro-1 H-indole (2.Og, 92%). The crude compound was used in the next stage without purification.

6146-52-7 5-Nitroindole 22523, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Patent; F2G LTD; WO2006/123145; (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

51417-51-7,51417-51-7, 7-Bromoindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 1: Synthesis of 2(E)-methyl3-(1H-indol-7-yl)acrylate 7-Bromoindole (5.0 g, 25.5 mmol), methyl acrylate (4.6 ml, 51.1 mmol), triphenylphosphine (0.55 g, 2.10 mmol), N,N-diisopropylethylamine (5.8 ml, 42.3 mmol), and palladium (II) acetate (0.25 g, 1.11 mmol) were added to N,N-dimethylformamide (50 ml), and the mixture was stirred at 70 C. for 18 hours under a stream of nitrogen. After cooling to room temperature, methyl acrylate (4.6 ml, 51.1 mmol), triphenylphosphine (0.55 g, 2.10 mmol), and palladium (II) acetate (0.25 g, 1.11 mmol) were added to the reaction mixture, and the mixture was stirred at 75 C. for 47 hours under a stream of nitrogen. After cooling to room temperature, methyl acrylate (7.0 ml, 77.7 mmol), triphenylphosphine (0.88 g, 3.36 mmol), and palladium (II) acetate (0.40 g, 1.78 mmol) were added to the reaction mixture, and the mixture was stirred at 100 C. for 95 hours under a stream of nitrogen. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. To the obtained residue, a hexane/ethyl acetate mixed solution (1:1, 300 ml) was added, and the organic layer was washed with water. The obtained aqueous layer was subjected to extraction with a hexane/ethyl acetate (1:1) mixed solution, and the combined organic layer was washed with saturated saline. The obtained organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography (eluent; hexane:ethyl acetate=6:1) to obtain 2 (E)-methyl 3-(1H-indol-7-yl)acrylate (3.46 g, 67%) as a pale yellow-brown solid. ESI-MS: m/z 202 [M+H]+. 1H-NMR (CDCl3) delta: 3.85 (3H, s), 6.52 (1H, d, J=16.0 Hz), 6.62 (1H, dd, J=2.9, 2.0 Hz), 7.16 (1H, t, J=7.6 Hz), 7.28 (1H, t, J=2.9 Hz), 7.43 (1H, d, J=7.6 Hz), 7.71 (1H, d, J=7.6 Hz), 8.04 (1H, d, J=16.0 Hz), 8.59 (1H, br s).

51417-51-7 7-Bromoindole 2757020, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Patent; ArQule, Inc.; US2012/165278; (2012); 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.1953-54-4,5-Hydroxyindole,as a common compound, the synthetic route is as follows.

EXAMPLE 10 Preparation of 4-(1H-indol-5-yloxy)-2-phenylthieno[2,3-b]pyridine-5-carbonitrile 130 A mixture of 4-chloro-2-phenylthieno[2,3-b]pyridine-5-carbonitrile 20 (120 mg, 0.44 mmol), 5-hydroxyindole (71 mg, 0.53 mmol) and potassium carbonate (91 mg, 0.66 mmol) in 4 mL of acetonitrile was heated at 80 C. for 5 hours. The reaction mixture was cooled and diluted with 10 mL of water. The precipitate was collected by filtration and washed with water followed by diethyl ether to give 127 mg (79%) of 4-(1H-indol-5-yloxy)-2-phenylthieno[2,3-b]pyridine-5-carbonitrile 130 as an off-white solid, mp 219-221 C., MS 368.1 (M+H)+., 1953-54-4

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

Reference£º
Patent; Boschelli, Diane H.; Cole, Derek C.; Asselin, Magda; Barrios Sosa, Ana C.; Wu, Biqi; Tumey, Lawrence N.; US2007/82880; (2007); 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

230291-43-7, Methyl 4-chloro-1H-indole-2-carboxylate is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of methyl 4-chloro-li -indole-2-carboxylate (5.30 g, 25.2 mmol) and potassium carbonate (10.4 g, 75.8 mmol) inN,N-dimethylformamide (70.0 mL) was added methyl iodide (10.7 g, 75.8 mmol) and the reaction mixture was stirred at 60 C for 4 hrs. On completion, the reaction mixture was concentrated in vacuo to give a crude product, which was purified by silica gel chromatography (petroleum ether : ethyl acetate = 5: 1) to give the title compound. NMR (400MHz, DMSO-d6) delta = 7.63 (d, J= 8.4 Hz, 1H), 7.36 (t, J= 8.0 Hz, 1H), 7.28 – 7.17 (m, 2H), 4.06 (s, 3H), 3.88 (s, 3H).

230291-43-7, The synthetic route of 230291-43-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; RAZE THERAPEUTICS, INC.; MAINOLFI, Nello; (358 pag.)WO2017/156165; (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

5192-23-4, 4-Aminoindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

EXAMPLE 19. N-(3-(9H-PURGammaN-6-YL)PYRIDGammaN-2-YL)- 1H-LNDOL-4-AMGammaNE [00165] 6-(2-Fluoropyridin-3-yl)-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (115.0 mg, 0.3842 mmol) and lH-indol-4-amine (Aldrich, St. Louis, MO, 70.7 mg, 0.535 mmol) were suspended in EtOH (1.8 mL) and aqueous hydrochoric acid (5.0 M, 0.090 ml, 0.45 mmol) was added. The flask was fitted with a reflux condenser and placed in a preheated oil bath (100 0C), and the reaction was stirred for 3 hours. Then, the reaction was cooled to room temperature and diluted with DCM, 2 N ammonia in MeOH, EtOH, and MeOH and concentrated. The residue was treated with MeOH and filtered. Neither the filtrate nor the solid contained pure material, so they were combined, concentrated, treated with DMF, and filtered. The filtrate was concentrated and purified on HPLC (10% to 100% MeCN / water with 0.1% TFA over 30 minutes with a total flow rate of 100 mL/min). The fractions with product were collected, concentrated, and filtered through a silica gel plug (about 1 inch, 50: 1 DCM / 2 N ammonia in MeOH to 20: 1 DCM / 2 N ammonia in MeOH to 5: 1 DCM / 2 N ammonia in MeOH) to afford N-(3-(9H-purin-6-yl)pyridin-2-yl)-lH-indol-4-amine (6.9 mg, 5% yield). MS (ESI pos. ion) m/z: 328, (M+H)+. 1H NMR (d6-DMSO, 400 MHz) delta 12.90 (s, IH), 11.16 (s, IH), 9.87 (d, J = 7.82 Hz, IH), 9.24 (s, IH), 8.73 (s, IH), 8.43 (dd, J = 4.69 Hz, 1.96 Hz, IH), 8.28 (dd, J = 4.6 Hz, 3.81 Hz, IH), 7.38 – 7.35 (m, IH), 7.09 (s, IH), 7.08 – 7.06 (m, IH), 7.04 (dd, J = 7.82 Hz, 4.69 Hz, IH), 6.79 – 6.76 (m, IH)., 5192-23-4

The synthetic route of 5192-23-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; AMGEN INC.; ANDREWS, Kristin; BO, Yunxin, Y.; BOOKER, Shon; CEE, Victor, J.; D’ANGELO, Noel; HERBERICH, Bradley, J.; HONG, Fang-Tsao; JACKSON, Claire, L., M.; LANMAN, Brian, A.; LIAO, Hongyu; LIU, Longbin; NISHIMURA, Nobuko; NORMAN, Mark, H.; PETTUS, Liping, H.; REED, Anthony, B.; SMITH, Adrian, L.; TADESSE, Seifu; TAMAYO, Nuria, A.; WU, Bin; WURZ, Ryan; YANG, Kevin; WO2010/126895; (2010); 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

51417-51-7,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.51417-51-7,7-Bromoindole,as a common compound, the synthetic route is as follows.

General procedure: Under a nitrogen stream, 5-bromo-1H-indole (25g, 0.128mol), 4,4,4?,4?,5,5,5?,5?-octamethyl-2,2?-bi(1,3,2-dioxaborolane)(48.58g, 0.191mol), Pd (dppf) Cl2 (5.2g, 5mol), KOAc (37.55g, 0.383mol), and 1,4-dioxane (500ml) mixed, and the mixture was stirred for 12 hours at 130C .After completion of the reaction, and extracted with ethyl acetate, water was removed by MgSO4, column chromatography (hexane: EA = 10: 1 (v / v)) purified to at 5- (4,4,5,5-tetra to give methyl 1,3,2-dioxaborolan-2-yl)-lH-indole (22.32g, 72% yield).7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indolewas obtained by performing the same procedure as in ofPreparation Example 1, except that 7-bromo-1H-indole was used insteadof 5-bromo-1H-indole.

The synthetic route of 51417-51-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; DOOSAN CORPORATION; PARK, HO CHEOL; BAE, HYUNG CHAN; EUM, MIN SIK; BEAK, YOUNG MI; LEE, CHANG JUN; SHIN, JIN YONG; KIM, TAE HYUNG; (163 pag.)JP2015/528445; (2015); 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

5192-23-4, 4-Aminoindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a stirred solution of 4-chloro-5-[3-(2-chloroethoxy)phenyl]-nicotinonitrile (200 mg, 0.68 mmol), 4-aminoindole (135 mg, 1 mmol), DavePhos (80 mg, 0.20 mmol), and K3PO4 (216 mg, 1 mmol) in 4 mL anhydrous ethylene glycol dimethyl ether was added Pd2(dba)3 (62 mg, 0.07 mmol). The mixture was heated at 90 C. for 2 h then cooled, filtered through celite, concentrated in vacuo, and purified by flash chromatography on silica gel eluting with a gradient of 5-50% MeOH in CH2Cl2 to yield 155 mg (59% yield) of 5-[3-(2-chloroethoxy)phenyl]-4-(1H-indol-4-ylamino)-nicotinonitrile 165 as a tan solid. MS: 389.1 (M+H), HPLC retention time: 9.60 min.(a)., 5192-23-4

The synthetic route of 5192-23-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Cole, Derek Cecil; Boschelli, Diane Harris; Wang, Yanong Daniel; Asselin, Magda; Joseph-McCarthy, Diane Marie; Prashad, Amarnauth Shastrie; Wissner, Allan; Dushin, Russell; Wu, Biqi; Tumey, Lawrence Nathan; Niu, Chuan S.; Chen, Joan; US2007/287708; (2007); 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.120-72-9,1H-Indole,as a common compound, the synthetic route is as follows.

To a solution of indole (10.021 g, 85 mmol) in diethyl ether (150 mL) was added oxalyl chloride (11.0 mL, 16.3 g, 0.13 mol) dropwise over 10 minutes and the yellow suspension was allowed to stir for a further 30 minutes at room temperature. Saturated aqueous sodium bicarbonate (20 mL) was then added with caution and the biphasic mixture was stirred for 16 hours. The product was then collected using vacuum filtration, washed with diethyl ether and dried overnight at 40 C to give a yellow solid (14.167 g, 88%): m.p. 193-196 C; (Lit. 210 C decomp.)47; numax/cm-1(KBr) 3549, 3195, 1719, 1611, 1268; deltaH(300 MHz, DMSO-d6) 7.26 [1H, ddd,J9.1, 7.1, 1.7, C(5)-H], 7.29 [1H, ddd,J9.3, 7.1, 1.9, C(6)-H], 7.52-7.58 [1H, m, C(7)-H], 8.14-8.20 [1H, m, C(4)-H], 8.42 [1H, d,J3.3, C(2)-H], 12.36 (1H, bs, N-H); m/z (ESI+) = 190.3 [(M+H)+100%]., 120-72-9

The synthetic route of 120-72-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Winfield, Hannah J.; Cahill, Michael M.; O’Shea, Kevin D.; Pierce, Larry T.; Robert, Thomas; Ruchaud, Sandrine; Bach, Stephane; Marchand, Pascal; McCarthy, Florence O.; Bioorganic and Medicinal Chemistry; vol. 26; 14; (2018); p. 4209 – 4224;,
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.244-69-9,5H-Pyrido[4,3-b]indole,as a common compound, the synthetic route is as follows.

Another reaction vessel was charged with 17.2 ml of 1,3-dibromobenzene, 6.0 g of 5H-pyrido[4,3-b]indole, 1.1 g of copper powder, 9.9 g of potassium carbonate, and 0.6 ml of dimethyl sulfoxide, followed by heating and stirring at 180C for 4 hours. After cooling to room temperature, 50 ml of chloroform was added thereto, the insoluble materials were removed by filtration and the filtrate was concentrated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography (carrier: silica gel, eluent: hexane/chloroform) to obtain 7.1 g (yield 62%) of 5-(3-bromophenyl)-5H-pyrido[4,3-b]indole as a white powder., 244-69-9

As the paragraph descriping shows that 244-69-9 is playing an increasingly important role.

Reference£º
Patent; Hodogaya Chemical Co., Ltd.; EP2241568; (2010); 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