Tag: M.W:100-200

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.

2795-41-7, A. 6-Fluoro-3-(2-nitropropenyl)-1 H-indole was prepared by combining 6-fluoroindole-3-carboxaldehyde (485 mg, 2.97 mmol), nitroethane (6.0 mL), and ammonium acetate (250 mg, 3.27 mmol). The reaction solution was allowed to reflux 2 hours. The reaction solution was diluted with EtOAc (100 mL), washed with H20 (50 mL x 2), partitioned, dried over Na2SO4, filtered, and concentrated under reduced pressure to provide 560 mg (86 % yield) of 6-fluoro-3-(2-nitropropenyl)-1H- indole ; 1H NMR (CDCI3) b 11.03 (1H, brs), 8.41 (1H, s), 7.63 (1H, dd), 7.50 (1H, s), 7.06 (1H, dd), 6.92 (1H, t), 2.44 (3H, s); TLC (SiO2 plate, 100 % DCM) Rif-0 7

2795-41-7 6-Fluoroindole-3-carboxaldehyde 262903, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; X-CEPTOR THERAPEUTICS, INC.; WO2003/99821; (2003); 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.

To a suspension of sodium hydride (60% dispersion in mineral oil, 2.14 g, 53.5 mmol) in dry N,N-dimethylformamide (30 mL) was added a solution of 4-fluoro-1H-pyrrolo[2,3-b]pyridine (5.77 g, 42.46 mmol) in dry N,N-dimethylformamide (58 mL) dropwise at 0 C. The mixture was stirred at 0 C for 15 min. To the mixture was added a solution of triisopropylsilyl chloride (10 mL, 46.71 mmol) in dry N,N-dimethylformamide (12 mL) dropwise at 0 C over 30 min. The reaction mixture was allowed to warm to room temperature and the mixture was stirred at room temperature for 42 h. The reaction mixture was poured into ice water (800 mL) and the mixture was extracted with dichloromethane (4 x 200 mL). The combined organic layers were washed with water (2 x 200 mL), dried over sodium sulfate, filtered and evaporated. The residue was purified by gradient silica gel column chromatography eluting with n-heptane:ethyl acetate (100:0 to 50:50) to afford the title compound (8.51 g, 29.14 mmol, 68%) as a pale yellow liquid. LCMS Method A: 99%, tR=2.242 min, m/z = 293.2 [M+H]+.

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

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

171879-99-5, 4-Chloro-6-methyl-7-azaindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Into a 50-mL round-bottom flask, was placed 4-chloro-6-methyl-lH- pyrrolo[2,3-b]pyridine (150 mg, 0.90 mmol, 1 equiv), 5-methoxy-4-[3-(pyrrolidin-l- yl)propoxy]pyridin-2-amine (228 mg, 0.91 mmol, 1 equiv), CS2CO3 (884 mg, 2.71 mmol, 3.00 equiv), Pd2(dba)3-CHC13 (50 mg), X-phos (50 mg), 1,4-dioxane (10 mL). The resulting solution was stirred for 4 h at 100 C. The crude product was purified by Flash-Prep-HPLC A 1 : 1. This resulted in 35.9 mg (9.5%) of N-(5-methoxy-4-(3-(pyrrolidin-l-yl)propoxy)pyridin- 2-yl)-6-methyl-lH-pyrrolo[2,3-b]pyridin-4-amine as a light yellow solid., 171879-99-5

As the paragraph descriping shows that 171879-99-5 is playing an increasingly important role.

Reference：
Patent; EPIZYME, INC.; CAMPBELL, John Emmerson; DUNCAN, Kenneth William; FOLEY, Megan Alene; HARVEY, Darren Martin; KUNTZ, Kevin Wayne; MILLS, James Edward John; MUNCHHOF, Michael John; (586 pag.)WO2017/181177; (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

101495-18-5, 4,6-Dichloro-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

4,6-dichloro-lH-indole (1 eq) was dissolved in DMF, K2COj (3eq) and 2-(3~ bromopropyl)isoindoline-l,3-dione (1.1 eq) was added and the mixture stirred at 60 C for 3 h. Solvent was removed and extracted with DCM. The organic extract was washed with water, brine and dried over Ma2S04. The residue was purified via flash chromatography on silica gel to obtain 2-(3-(4,6-dich3oro- lH-indoi-l-yr)propyi)isoindoline- .l,3-dione.

101495-18-5, As the paragraph descriping shows that 101495-18-5 is playing an increasingly important role.

Reference：
Patent; UNIVERSITY OF WASHINGTON; BUCKNER, Frederick, S.; ALVAREZ, Ximena, Barros; FAN, Erkang; GILLESPIE, John, Robert; HOL, Wilhelmus, G.J.; HUANG, Wenlin; KOH, Cho, Yeow; RANADE, Ranae, M.; SHIBATA, Sayaka; VERLINDE, Christophe, L.M.; ZHANG, Zhongsheng; (249 pag.)WO2016/29146; (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

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

General procedure: A method for synthesizing compound III-1 wherein R1, R2 and R3 are simultaneously hydrogen in the formula III, the method comprising the steps of:(1) Add to a 50 mL round bottom flask1.0mmol indole(In the formula I, R1, R2, and R3 are both hydrogen) and1.0 mmol (0.140 g) of hexamethylenetetramine, then 2 mL of N,N-dimethylformamide (DMF), stirred in a magnetic stirrer to dissolve the solid, followed by the addition of 0.05 mmol (0.012 g) of crystalline trichloride Aluminum, connected to a reflux condenser, heated at 120 C, the reaction progress was monitored by TLC, and the reaction was cooled to room temperature after 1 h to prepare a suspension;(2) The suspension prepared in the step (1) is suction filtered with a funnel padded with diatomaceous earth.The filter cake was washed well with ethyl acetate, suction filtered, and the above operation was repeated until the filtrate had no product, and all the filtrates were combined.Dilute with 15 mL of saturated saline solution, disperse and separate the layers, and the aqueous layer was further extracted with ethyl acetate three times.Each time 10 mL, the ethyl acetate layer was combined and washed with 10 mL of 2 mol/L diluted hydrochloric acid.Wash with 10 mL of saturated sodium bicarbonate solution, and finally wash with 10 mL of saturated brine.The washed ethyl acetate layer was dried over anhydrous sodium sulfate, and after drying, the desiccant was filtered off.Then use a rotary evaporator to recover the solvent to concentrate the product, and finally,The residue is subjected to silica gel column chromatography using a mixture of n-hexane-ethyl acetate (V/V = 2:1) as an eluent to obtain a purified product.The mass of the compound III-indole-3-carbaldehyde is 0.137g,The product yield was 94%., 399-51-9

As the paragraph descriping shows that 399-51-9 is playing an increasingly important role.

Reference：
Patent; Yancheng Jin Ming Pharmaceutical Co., Ltd.; Yancheng Normal College; Wang Qingdong; Yang Zijian; Fang Yue; Wu Zhen; Zeng Bubing; Yang Jinming; Hu Chaojun; Zhao Yujun; (19 pag.)CN108329249; (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

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

879-37-8, EXAMPLE 1 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)pyrrole-2,5-dione [0441] To a 0 C. solution of 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)oxoacetic acid methyl ester (0.5 g, 2.06 mmol) and indole-3-acetamide (0.394 g, 2.26 mmol) in 10 mL of tetrahydrofuran was added dropwise potassium tert-butoxide (16.4 mL, 16.4 mmol, 1 M in tetrahydrofuran). Following 2 hours at 0 C., 5.0 mL of concentrated hydrochloric acid was added and the reaction mixture stirred at room temperature for 1 more hour. The mixture was diluted with 100 mL of ethyl acetate, and the organic layer washed with water (2×25 mL), saturated aqueous sodium chloride (25 ml), dried over sodium sulfate, filtered and concentrated in vacuo. The residue was subjected to silica gel chromatography, eluting with a gradient of dichloromethane containing from 1-5% methanol. Fractions containing product were combined and concentrated under reduced pressure to provide 0.598 g (79%) of the title compound as a red solid. [0442] MS (IS, m/z) C23H17N3O2 (M++1)=368.

As the paragraph descriping shows that 879-37-8 is playing an increasingly important role.

Reference：
Patent; Al-Awar, Rima Salim; Hecker, Kyle Andrew; Ray, James Edward; Huang, Jianping; Joseph, Sajan; Li, Tiechao; Paal, Michael; Rathnachalam, Radhakrishnan; Shih, Chuan; Waid, Philip Parker; Zhou, Xun; Zhu, Guoxin; US2003/229026; (2003); 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.39689-58-2,2-(1H-Indol-6-yl)acetic acid,as a common compound, the synthetic route is as follows.

(Naruto, S. and Yonemitsu, O. Chem. Pharm. Bull. 1972, 20, 2163.) (118.5 mg, 0.676 mmol), (lR)-l-{5-[(2,2,2-trifluoroethyl)oxo]pyridin-2-yl}ethylamine dihydrochloride (198.0 mg, 0.676 mmol), l-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (143 mg, 0.744 mmol), l-hydroxy-7-azabenzotriazole (101 mg, 0.744 mmol) and diisopropylethylamine (0.295 ml, 1.691 mmol) into 1.4 ml of DMF. The resulting solution was stirred at room temperature for 1 hour. The reaction mixture was purified by reverse-phase etaPLC to give 2-(l//-indol-6-yl)-7V- {(lR)-l-[5-(2,2,2-trifluoroethoxy)pyridin-2-yl]ethyl}acetamide 229 mg as a TFA salt (69%). 1H NMR (CDCl3, 400 MHz) delta 8.29 (d, J= 2.8 Hz, IH), 8.28 (m, IH), 7.57 (d, J= 8.0 Hz, IH), 7.46 (dd, J= 2.4, 8.8 Hz, IH), 7.42 (d, J= 8.8 Hz, IH), 7.37 (d, J= 7.2, IH), 7.30 (s, IH), 7.19 (dd, J = 2.8, 3.2 Hz, IH), 6.98 (dd, J= 1.6, 8.4Hz, IH), 6.53-6.51 (m, IH), 5.12 (quintet, J= 7.2 Hz, IH), 4.38 (q, J= 8.0 Hz, 2H), 3.66 (s, 2H), 1.47 (d, J= 7.2 Hz, 3H); HRMS (ES) [M+l]+ calcd for C9Hi9F3N3O2: 378.1424, Found: 378.1439., 39689-58-2

The synthetic route of 39689-58-2 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; MERCK & CO., INC.; WO2009/54983; (2009); 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

23872-36-8, 4-Chloro-1H-indole-3-carboxylic acid is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 1 Preparation of 4-Chloro-1-dimethylcarbamoylmethyl-1H-indole-3-carboxylic acid 2-chloro-N,N-dimethylacetamide (0.19 ml; 1.84 mmol; 1.20 eq.) was added to a solution of 4-Chloro-1H-indole-3-carboxylic acid (300.00 mg; 1.53 mmol; 1.00 eq.) and barium hydroxide octahydrate (967.67 mg; 3.07 mmol; 2.00 eq.) in DMF (15.63 ml; 202.65 mmol; 132.13 eq.) at 50° C. The reaction mixture was stirred overnight. The reaction mixture was diluted with DMSO (1 ml) and water (1 ml) then submitted to MPLC purification (Yamazen, Interchim 100 g polymeric Reverse Phase column, basic buffer) to afford the desired product 4-Chloro-1-dimethylcarbamoylmethyl-1H-indole-3-carboxylic acid (426.00 mg; 1.52 mmol) as a white solid. 1H NMR (400 muMHz, MeOD) delta 7.42 (s, 1H), 6.89-6.79 (m, 1H), 6.78-6.64 (m, 2H), 4.73 (s, 2H), 2.73 (s, 3H), 2.57-2.49 (m, 4H) ppm; [M+H]+ 281.1. LC-MS (254 nm) tR=3.47 min; HPLC (254 nm) Purity: >99percent; tR=2.68 min.

23872-36-8, As the paragraph descriping shows that 23872-36-8 is playing an increasingly important role.

Reference：
Patent; Merck Patent GmbH; KARRA, Srinivasa R.; (153 pag.)US2016/168090; (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

39689-58-2, 2-(1H-Indol-6-yl)acetic acid is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,39689-58-2

To a solution of the compound [4-5] obtained in the process (5) (497 mg) in N,N-dimethylformamide (10 mL) were added potassium carbonate (511 mg) and methyl iodide (0.12mL) at 0C, and then the reaction mixture was stirred at room temperature for 13 hours. The reaction mixture was quenched with water, and extracted with ethyl acetate. The obtained organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the titled compound (512 mg) as a white solid. 1H-NMR (400MHz, CD3 OD) delta: 8.25-8.00 (1H,br), 7.59 (1H,d, J = 8.1 Hz), 7.33 (1H,d, J = 0.7 Hz), 7.19 (1H,t, J = 2.8 Hz), 7.04 (1H, dd, J = 8.1, 1.2 Hz), 6.53 (1H, s), 3.73 (2H, s), 3.69 (3H, s).

39689-58-2 2-(1H-Indol-6-yl)acetic acid 14882503, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; Sato Pharmaceutical Co., Ltd.; NAGAI Keita; NAGASAWA Koh; TAKAHASHI Hirobumi; BABA Motoaki; FUJIOKA Shinichi; KONDOH Eri; TANAKA Kenichi; ITOH Yoshiki; EP2669270; (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.32588-36-6,Indole-2-acetic acid,as a common compound, the synthetic route is as follows.

To a solution of compound 7 (100mg, 0.25 mmol)and 2-(1H-indol-2-yl)acetic acid (44 mg, 0.25 mmol) in 5 mlDMF was added HOAT (68 mg, 0.50 mmol), EDCI (78 mg,0.50 mmol) and DIPEA (129 mg, 1 mmol). The mixture wasstirred at 60 C. overnight, LCMS monitored the reaction tocompletion. The target compound 8 (80 mg, 766%) wasobtained as a yellow solid following extraction with EA andfiltration through silica gel.

32588-36-6, As the paragraph descriping shows that 32588-36-6 is playing an increasingly important role.

Reference：
Patent; Acetylon Pharmaceuticals, Inc.; Jones, Simon Stewart; Yang, Min; Tamang, David Lee; US2015/105384; (2015); 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