Day: March 23, 2022

165250-69-1, 4-Methyl-5-nitro-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a cooled solution (ice-water bath) of 4-methyl-5-nitroindole (1.76 g, 10 mmol) in DMF (30 mL) was added KOH pellets (0.78 g, 14 mmol). The cooling bath was removed, and the mixture was stirred at rt for 10 min. Iodine (2.79 g, 11 mmol) was added, and the stirring was continued for 5 h at room temperature. To this mixture was added potassium carbonate (3.17 g, 23 mmol) and methyl iodide (3.1 mL, 50 mmol), and stirring was continued at room temperature for 16 h. The mixture was diluted with water (150 mL), and treated with solid NaHSO3 with stirring until all excess iodine was quenched. The crude product was collected by filtration, washed with plenty of water, and dried.

165250-69-1, The synthetic route of 165250-69-1 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; PFIZER INC.; Schnute, Mark Edward; Wennerstal, Goeran Mattias; Blinn, James Robert; Kaila, Neelu; Kiefer, JR., James Richard; Mente, Scot Richard; Kurumbail, Ravi G.; Meyers, Marvin Jay; Thorarensen, Atli; Xing, Li; Zapf, Christoph Wolfgang; Zamaratski, Edouard; Flick, Andrew Christopher; Jones, Peter; (77 pag.)US2016/46597; (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

1065181-58-9, Ethyl 5-bromo-1H-indole-7-carboxylate is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Intermediate 72:(racem/cJ-Ethyl 5-bromo-3-(2,2-dimethyltetrahydro-2H-thiopyran-4-yl)-1H-indole-7- carboxylate.2,2-Dimethyltetrahydro-4H-thiopyran-4-one (0.675 g, 4.68 mmol) was placed in a dried flask fitted up with an addition funnel, a septum and an argon inlet, and dissolved in dry DCM (15 mL), cooled to 0 0C, stirred, and then trimethylsilyl trifluoromethanesulfonate (1.692 mL, 9.36 mmol) was added dropwise through the addition funnel over 10 minutes. DCM (5 mL) was used to wash the addition funnel walls. To this mixture was added dropwise ethyl 5-bromo-1 H-indole-7- carboxylate (1.341 g, 5 mmol) in DCM (15 mL) over 2 hours. Then triethylsilane (2.98 mL, 18.73 mmol) was added in one portion. The mixture was stirred 2 h at 0 0C, and left stirring at 23 0C overnight. The reaction was quenched with a saturated aqueous solution of sodium bicarbonate, and the resulting biphasic mixture extracted with DCM to give 2.1 15 g of the title compound. LC/MS: m/z 398.0 (M+H), Rt 1.49 min., 1065181-58-9

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

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

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

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

170147-29-2, tert-Butyl 5-(benzyloxy)-1H-indole-1-carboxylate is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of scheme 6-6 compound S2 (2 g, 6.19 mmol) in MeCN (40 mL) at 0 C was added chlorosulfonyl isocyanate dropwise (0.57 mL, 6.50 mol). The reaction was stirred at room temperature overnight and then acetone (40 mL) and H20 (5 mL) was added followed by dropwise addition of 10% aq.KOH solution (2 mL). The mixture was stirred at room temperature for 30 mm and extracted with ethyl acetate (50 mL x 2). The combined organic phases were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to dryness. The residue was further washed with EtOAc to give the title compound (1.7 g, 75% yield) as a white solid. LC/MS (ESI) m/z: 311 (M-56+H) +, 170147-29-2

170147-29-2 tert-Butyl 5-(benzyloxy)-1H-indole-1-carboxylate 10663688, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason Allan; PHADKE, Avinash S.; DESHPANDE, Milind; AGARWAL, Atul; CHEN, Dawei; GADHACHANDA, Venkat Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; GREENLEE, William; (358 pag.)WO2017/35411; (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

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