Month: March 2022

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

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.1065181-58-9,Ethyl 5-bromo-1H-indole-7-carboxylate,as a common compound, the synthetic route is as follows.,1065181-58-9

Intermediate 98:Ethyl 5-bromo-3-(tetrahydro-2H-thiopyran-3-ylmethyl)-1H-indole-7-carboxylate.To a 100 ml. three-necked flask equipped with an addition funnel was added tetrahydro- 2H-thiopyran-3-carbaldehyde (2.50 g, 0.019 mol) and dry DCM (30 ml_). Trimethylsilyl trifluoromethanesulfonate was put in the addition funnel. The mixture was cooled down to0 0C with an ice bath and put under nitrogen atmosphere. Trimethylsilyl trifluoromethanesulfonate was added over 15 min, and 10 ml. of dry DCM were used to wash the addition funnel walls. A solution of ethyl 5-bromo-1 H-indole-7-carboxylate in 30 ml. dry DCM was added to the mixture for 2 h at 0 0C, and the mixture was then stirred at room tmperature overnight. An aqueous solution of sodium bicarbonate was added, the layers were separated, and the mixture was extracted with DCM (3 x 100 ml_). The combined organic layers were dried (Na2SO4), filtered, and purified by chromatography, eluting with a mixture of PE:EA (50:1-30:1 ) to afford 4.82 g (66.0%) of the title compound. 1H NMR NMR (CDCI3) delta 1.1 1-1.15 (m,1 H),1.43 (t,3H),1.65-1.71 (m,2H),1.83-1.87 (m,1 H),1.96-2.03 (m,2H), 2.32-2.38 (m,1 H), 2.51-2.59 (m, 2H),2.66-2.68 (m, 2H), 4.40-4.45 (q,2H), 7.07 (d, 1 H),7.77 (d, 1 H), 7.95 (d, 1 H), 9.64 (s, 1 H).

The synthetic route of 1065181-58-9 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/118724; (2008); 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

16732-69-7, Ethyl 7-bromo-1H-indole-2-carboxylate is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

c (R)-7-Bromo-1-(2-tert-butoxycarbonylamino-1-methyl-ethyl)-1H-indole-2-carboxylic acid ethyl ester A solution of 8.1 g (30.1 mmol) 7-bromo-1H-indole-2-carboxylic acid ethyl ester in 120 ml N,N-dimethylformamide was cooled to 0 C. and 3.55 g (31.6 mmol) potassium tert-butoxide was added. After 30 min., 7.86 g (33.1 mmol) (S)-5-methyl-2,2-dioxo-[1,2,3]oxathiazolidine-3-carboxylic acid tert-butyl ester were added and the cooling bath was removed. After 20 h the reaction mixture was poured on 10% aqueous citric acid solution and ethyl acetate. The organic layer was dried over magnesium sulfate, filtered and evaporated. The resulting yellow oil was chromatographed on silica gel (0.032-0.063 mm) with tert-butyl methyl ether: n-hexane (1:8) as eluant to give the desired compound as a yellow oil. ISP-MS: m/e=427.3 ([M+H+])., 16732-69-7

The synthetic route of 16732-69-7 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Hebeisen, Paul; Mattei, Patrizio; Muller, Marc; Richter, Hans; Roever, Stephan; Taylor, Sven; US2002/169163; (2002); 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

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

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

434958-85-7, N-Boc-5-Hydroxyindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 558 52 mg of tert-butyl 5-hydroxy-1H-indole-1-carboxylate, 79 mg of tripotassium phosphate, 4.7 mg of 2-(di-tert-butylphosphino)-2′,4′,6′-triisopropylbiphenyl and 6.8 mg of tris(dibenzylideneacetone)dipalladium(0) were added to 1.4 mL of toluene solution containing 70 mg of tert-butyl 2-(benzamido)-4-bromobenzoate at room temperature, and the resulting mixture was heated to reflux under nitrogen atmosphere for 2 hours and 30 minutes. After the reaction mixture was cooled to room temperature, ethyl acetate and 10% citric acid aqueous solution were added and insoluble were removed by filtration. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with a saturated sodium chloride aqueous solution, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [PSQ100B (spherical) manufactured by Fuji Silysia Chemical Ltd., eluent; hexane: ethyl acetate = 10:1] to obtain tert-butyl 5-(3-(benzamido)-4-(tert-butoxycarbonyl)phenoxy)-1H-indole-1-carboxylate., 434958-85-7

The synthetic route of 434958-85-7 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; TOYAMA CHEMICAL CO., LTD.; EP1820795; (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

1145678-74-5, (1-Tosyl-1H-indol-4-yl)methanamine is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,1145678-74-5

step 4: A tube was charged with 53 (415 mg, 1.38 mmol), 46 (486 mg, 2.07 mmol), DIPEA (1.0 ml) and IPA (3 mL), degassed, sealed and heated at 120 C overnight. The mixture was concentrated in vacuo. The residue was purified by Si02 chromatography eluting with a DCM/MeOH gradient (3.3 to 5%> MeOH) to afford 330 mg (48%) of N4-(5-cyclopropyl-lH-pyrazol-3-yl)- N2-((l-tosyl-lH-indol-4-yl) methyl) pyrimidine-2,4-diamine (50) as yellow solid: MS (ESI) m/z = 500.3 [M+l] +.

The synthetic route of 1145678-74-5 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; F. HOFFMANN-LA ROCHE AG; ALIAGAS-MARTIN, Ignacio; CRAWFORD, James; LEE, Wendy; MATHIEU, Simon; RUDOLPH, Joachim; WO2013/26914; (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