Tag: M.W:100-200

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.5192-03-0,1H-Indol-5-amine,as a common compound, the synthetic route is as follows.

A mixture of 2-amino-4,6-dichloropyrimidine (1.64 g, 10 mmol), 5-aminoindole (1.32 g, 10 mmol), diisopropylethylamine (5.23 ml, 30 mmol) and N,N-dimethylformamide (30 ml) was heated at 60C and stirred overnight under nitrogen atmosphere. The reaction mixture was partitioned between ethyl acetate and water after cooled to room temperature; and the organic layer was washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was distilled off; the obtained residue was dissolved in tetrahydrofuran (100 ml); 10% Palladium on carbon (50% wet, 1.0 g) was added thereto under nitrogen atmosphere; and the reaction mixture was stirred for 4 days under hydrogen atmosphere at atmospheric pressure. The reaction system was purged with nitrogen; the catalyst was filtered off; the filtrate was concentrated under reduced pressure; the residue was purified by NH silica gel column chromatography (eluent; ethyl acetate: methanol = 95: 5); diethyl ether was added to the residue to crystallize; and the crystals were filtered off, and dried under aeration to yield the title compound (852 mg, 3.8 mmol, 38%) as pale brown crystals. 1H-NMR Spectrum (DMSO-d6) delta (ppm): 5.89 (1H, d, J=5.6 Hz), 5.99 (2H, brs), 6.34 (1H, s), 7.12 (1H, d, J=8.4 Hz), 7.20-7.40 (2H, m), 7.70 (1H, d, J=5.6 Hz), 7.79 (1H, s), 8.73 (1H, s), 10.95 (1H, s).

5192-03-0, 5192-03-0 1H-Indol-5-amine 78867, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; Eisai Co., Ltd.; EP1522540; (2005); 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

31241-19-7, 5-Methoxy-2,3,3-trimethyl-3H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A synthetic procedure was based on the literature method [15] with some modifications. A solution of 5-methoxy-2,3,3-trimethyl-3H-indole (0.502 g, 1.60 mmol) and 2-bromoethanol (0.198 g, 2.00 mmol) in MeCN (20 mL) was maintained under N2 and heated under reflux for 1 day. After the mixture was cooled to ambient temperature, the solvent was distilled off under reduced pressure. The resulting solid was recrystallized from CHCl3 (35 mL), then filtered and dried, to afford the targeted compound in high yield (68%)., 31241-19-7

31241-19-7 5-Methoxy-2,3,3-trimethyl-3H-indole 11095392, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Article; Li, Hong; Pang, Meili; Wu, Bianpeng; Meng, Jiben; Journal of Molecular Structure; vol. 1087; (2015); p. 23 – 29;,
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

935269-27-5, 3-Oxoisoindoline-4-carboxylic acid is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

935269-27-5, Compound 16f was treated with 4-methoxy-benzene-l,2-diamine in 6N HCl to provide Compound 11. 1H NMR (400 MHz, MeOD) 3.87 (s, 3H), 4.56 (s, 2H), 6.92 (d, J = 8.7 Hz, IH), 7.15 (s, IH), 7.55 (broad s, IH), 7.65 (d, J = 7.6 Hz, IH), 7.75 (t, J = 7.6 Hz, IH), 8.56 (d, J = 7.6 Hz, IH); MS (ESI) m/z: 280 (MH+).

935269-27-5 3-Oxoisoindoline-4-carboxylic acid 44579994, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; JANSSEN PHARMACEUTICA, N.V.; WO2007/47646; (2007); 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

399-67-7, 7-Fluoro-1H-indole-2-carboxylic acid is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: (5-Chloro-7-fluoro-1H-indole-2-yl)-carboxylic acid (5a) (50 mg, 0.23 mmol), N,N-diisopropylethylamine (82 mul, 0.47 mmol) and 2-(7-Aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (89 mg, 0.23 mmol) were dissolved in 550 mul N,N-dimethylformamide. After stirring for 10 min 4-methyl-piperazin 6a (26 mul, 0.23 mmol) was added and the reaction mixture was stirred for 16 h at 20 C. The solvent was evaporated under reduced pressure and the crude product was purified using chromatography method P1, yielding 37 mg (53%) of the title compound., 399-67-7

As the paragraph descriping shows that 399-67-7 is playing an increasingly important role.

Reference：
Article; Engelhardt, Harald; De Esch, Iwan J.P.; Kuhn, Daniel; Smits, Rogier A.; Zuiderveld, Obbe P.; Dobler, Julia; Mayer, Moriz; Lips, Sebastian; Arnhof, Heribert; Scharn, Dirk; Haaksma, Eric E.J.; Leurs, Rob; European Journal of Medicinal Chemistry; vol. 54; (2012); p. 660 – 668;,
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.7506-66-3,cis-Hexahydro-1H-isoindole-1,3(2H)-dione,as a common compound, the synthetic route is as follows.

7506-66-3, To the crude spiro quaternary ammonium hydroxide mixture (280g) was added Example 1 cis-dimethyl cyclohexane imide (84.8g) in MIBK (1272ml) suspension. Under vigorous stirring refluxing, the reaction system after water net, the reaction system temperature was lowered to 50 C-60 C, weighed DMAC (181 g) into the reaction mixture, continue to heat refluxing 7-10 hour. After completion of the reaction and the DMAC MIBK was distilled off, do not pay attention to the reaction system temperature above 135 C, above 135 C after distillation under reduced pressure to remove the DMAC and MIBK, in addition to the net after, the reaction liquid was boiled in boiling water 5- 10 minutes, filtered and cooled, this operation repeated 2-3 times to remove the reaction product mixture of inorganic salts. When, after the remaining material was added ethanol (400ml), at 20 C_40 C conditions, hydrogen chloride gas for 30 minutes to saturation, then refluxed for 30 minutes, concentrating the reaction solution, a large number of crystallization, cooling is cooled until crystallization , crude 175g. The precipitate was available in 95% ethanol was recrystallized as white needles after recrystallization of perospirone hydrochloride (134g). The total product yield was 69.95%, 99.85% purity liquid.

7506-66-3 cis-Hexahydro-1H-isoindole-1,3(2H)-dione 6992236, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; Yantai Besten Pharmaceutical Co., Ltd.; Bi, Haidong; Zhang, Yifang; (8 pag.)CN105669665; (2016); 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, To a solution of 0.38 g (2.3 mmol) 6-chloro-2-methyl-1H-indole in 20 ml 1,2-dichloroethane at 0 C. were added 0.35 ml (2.5 mmol) trifluoroacetic anhydride. The reaction mixture was quenched with aqueous 2 M sodium carbonate solution after 30 min and extracted with dichloromethane (3*100 ml). The combined organic layers were dried over sodium sulfate and concentrated in vacuo to give the title compound (0.57 g; 95%) as an off-white solid. MS m/e (%): 260 (M-H+, 100).

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

Reference：
Patent; Bissantz, Caterina; Grundschober, Christophe; Ratni, Hasane; Rogers-Evans, Mark; Schnider, Patrick; US2007/27173; (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

61019-05-4, 5-Methoxy-7-methyl-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

61019-05-4, To a 250 ml round bottom flask was added 7-methyl-5-methoxy-lH-indole (50 mmol)Add 100 ml of toluene to mix it,Further addition of cinnamoyl chloride (60 mmol)Room temperature reaction for 1 hour,After the compound has been completely precipitated,Phenylhydrazine (60 mmol) was added,Heated to 105 C with a heating jacket,Placed on a magnetic stirrer,The reaction was heated under reflux for 6 hours,Reaction process constantly point observation,After the reaction is complete, the heating is stopped and the condensing unit is removed.The reaction solution was distilled and concentrated, and the product was isolated by column chromatography.The crude product was recrystallized from an ethanol-water solution, dried,The product was obtained (pale pink solid 12.71 g, yield 80.2%).

As the paragraph descriping shows that 61019-05-4 is playing an increasingly important role.

Reference：
Patent; Shaanxi University of Science and Technology; Liang Chengyuan; Song Huihui; Zhang Shiyun; Mao Gennian; (17 pag.)CN104230786; (2017); 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

879-37-8,879-37-8, Indole-3-acetamide is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To compound C, indole-3-acetamide (104.71 g) and THF (1428 mL) were added at about 15 C. to about 35 C. under a nitrogen atmosphere. The resulting solution was added dropwise in the range of about 20 C. to about 32 C. over about 30 minutes or longer under a nitrogen atmosphere to a 1 M solution of potassium tert-butoxide in THF (1382.5 mL) further diluted with THF (420 mL). The reaction solution was stirred at about 20 C. to about 32 C. for about 2 hours. Then, 12 M hydrochloric acid (312 mL) was added dropwise at about 50 C. or lower, and the mixture was stirred at about 40 C. to about 50 C. for about 1 hour. After the completion of reaction, water (465 mL) and 28% ammonia water (465 mL) were added to the reaction solution, and the mixture was stirred at about 20 C. to about 32 C. for about 30 minutes or longer and then separated into aqueous and organic layers. The aqueous layer was removed. The organic layers containing compound B were combined and concentrated to about 2100 mL under a reduced pressure at an internal temperature of about 60 C. or lower. Ethanol (4095 mL) was added to the concentrated solution containing compound B. The resulting solution containing compound B was further concentrated to about 2100 mL under a reduced pressure at about 60 C. or lower, and then, ethanol (1050 mL) was added. The solution was concentrated to about 2100 mL under a reduced pressure at about 60 C. or lower to adjust the THF concentration to 2% or less. The concentrated solution obtained was cooled to about 20 C. to about 30 C., and water (2100 mL) was added dropwise over about 1 hour or longer. The resulting mixture containing compound B was stirred at about 20 C. to about 30 C. for 1 hour. The deposited crystals of compound B were collected by filtration and washed with a 50% aqueous ethanol solution (1050 mL). The crystals of compound B were dried in vacuum at about 45 C. to about 55 C. for about 12 hours or longer (178.7 g, yield: 80.9% (calculated based on indole-3-acetamide)). The crystals of compound B thus obtained can be used directly in next step. The crystals of compound B may be further purified as follows: methylene chloride (750 mL) was added to the crystals of compound B (150.0 g), and the mixture was stirred at about 15 C. to about 25 C. for about 2 hours or longer. To this suspension containing compound B, heptane (750 mL) was added dropwise at about 15 C. to about 25 C. over about 1 hour or longer, and the mixture was stirred at about 15 C. to about 25 C. for about 2 hours or longer. The deposited crystals of compound B were collected by filtration and washed with a mixed solvent of methylene chloride and heptane (mixing ratio: 1/1) (450 mL). The crystals of compound B were dried in vacuum at about 45 C. to about 55 C. for about 12 hours or longer (146.1 g, yield from crystals before purification: 97.4%).

The synthetic route of 879-37-8 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; ARQULE, INC.; Nakamura, Yoshitaka; Ooyama, Jo; US2013/281699; (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.171879-99-5,4-Chloro-6-methyl-7-azaindole,as a common compound, the synthetic route is as follows.

To a solution of 4-chloro-6-methyl-lH-pyrrolo[2,3-]pyridine (0.5 g, 3 mmol) in MeCN (15 mL) was added 2,6-difluorobenzylamine (2 eq) and pTSA.H20 (2 eq) under N2 at room temperature. The reaction mixture was heated at 150 C in a CEM microwave reactor for 4 hours. The mixture was diluted with sat. aq. NaHC03 (20 mL) solution and EtOAc (20 mL). The organic layer was separated, washed with brine, dried over MgSC^ and concentrated in vacuo. The residue was purified via flash chromatography using MeOH and DCM as eluent to give the product (0.521 g, 1.90 mmol, 63%) as yellow solid. 1H NMR (399 MHz, DMSO-d6) delta 10.96 (s, 1H), 7.43 (tt, 1H), 7.20 – 7.08 (m, 2H), 6.95 (d, 1H), 6.77 (t, 1H), 6.53 (d, 1H), 6.15 (s, 1H), 4.44 (d, 2H), 2.35 (s, 3H)., 171879-99-5

171879-99-5 4-Chloro-6-methyl-7-azaindole 24729584, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; LES LABORATOIRES SERVIER; VERNALIS (R&D) LIMITED; FIUMANA, Andrea; FOLOPPE, Nicolas; RAY, Stuart; WALMSLEY, David; KOTSCHY, Andras; BURBRIDGE, Michael, Frank; CRUZALEGUI, Francisco, Humberto; (141 pag.)WO2017/55533; (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

640735-23-5,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.640735-23-5,4-Fluoro-7-azaindole,as a common compound, the synthetic route is as follows.

[0723] To a stirred solution of 4-fluoro-1H-pyrrolo [2,3-bj pyridine (1.4 g, 10 mmol) in DMF (42 mL) at 0 C under an argon atmosphere were added potassium carbonate (2.1 g, 15 mmol) and methyl iodide (1.75 g, 12 mmol). The reaction mixture was warmed to room temperature and stirred for 12 h. After consumption of starting material (by TLC), the reaction mixture was diluted with water (100 mL) and extracted with EtOAc (2 x 50 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by column chromatography using 15%EtOAc:Hexane to afford 4-fluoro-1-methyl-1H-pyrrolo [2,3-bj pyridine (700 mg, 45%) as pale brown liquid. ?H NMR (CDC13, 400 MHz): 8.26 (dd, 1H), 7.12 (d, 1H), 6.78 (dd, 1H), 6.51 (d, 1H), 3.90 (s, 3H); TLC: 20% EtOAc Hexane (Rj: 0.5).

The synthetic route of 640735-23-5 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; FORUM PHARMACEUTICALS INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; HARRISON, Bryce, Alden; (273 pag.)WO2017/31325; (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