Month: March 2022

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.399-51-9,6-Fluoro-1H-indole,as a common compound, the synthetic route is as follows.

Place 40 ml DMF in a round bottom flaskSlowly add 6.89 ml of POCl3 (phosphorus oxychloride) under ice bath.After dropping,After stirring in an ice bath for 35 minutes,At a constant pressure dropping funnel was slowly added 5g6- fluoro indole in DMF,Stir at 35 C for 40 min.The reaction solution gradually changed from colorless to red.TLC shows that after the reaction is completed,Add 100ml of 19.3mmol/L aqueous NaOH,Stir vigorously for 30 minutes at 80C.Cool the reaction solutionAdd ethyl acetate extraction,30ml each time,A total of three extractions.Organic layers merge,After drying over anhydrous sodium sulfate,Evaporated to drynessSilica gel column chromatography 4.5g Intermediate I-1 (white solid, yield75%)., 399-51-9

The synthetic route of 399-51-9 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Hu Youhong; Geng Meiyu; Xing Weiqiang; Ding Jian; Ai Jing; (86 pag.)CN103664895; (2018); 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

1008-07-7, 7-Chloro-1H-indole-3-carbaldehyde is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

1008-07-7, Compound 1b (1.0 mmol, 177 mg) was added to a 25 mL sealed tube.Compound 2j (0.5 mmol, 89.8 mg), iodine (0.5 mmol, 127 mg),Pyridine (0.5 mmol, 39.6 mg) and 1,4-dioxane (2 mL),The reaction was then stirred in an oil bath at 110 C for 12 h. The reaction was quenched by the addition of 50 mL EtOAc (EtOAc)The organic phase was washed successively with a Na2S2O3 solution having a mass concentration of 10% and saturated brine, and dried over anhydrous sodium sulfate. Filter, spin dry,Separated by silica gel column(petroleum ether/ethyl acetate = 10/1, v/v)The white solid product 3u (112.4 mg, 59%) was obtained.

The synthetic route of 1008-07-7 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Xinxiang Medical University; Gao Qinghe; Liu Xingxia; Yuan Huan; Wang Yakun; Tong Peiyuan; Shen Haotian; Zhang Zhiang; Zhang Weirong; Zhang Jixia; (22 pag.)CN108976198; (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

288385-93-3, 4-Fluoro-5-methoxy-2-methyl-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Cleavage of 4-fluoro-5-methoxy-2-methylindole with boron tribromide to give 4-fluoro-5-hydroxy-2-methylindole is described above.

288385-93-3, The synthetic route of 288385-93-3 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Hennequin, Laurent Francois Andre; US2003/199491; (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.90924-06-4,1-Methyl-4-indolecarboxylic Acid,as a common compound, the synthetic route is as follows.

Example 2.4: (S)-N-(3-(N.1-dimethyl-1H-indole-4-carboxamido)-4-phenylbutyl)-1- methyl-1H-benzord1imidazole-2-carboxamide1-Methyl-1 H-benzoimidazole-2-carboxylic acid ((S)-3-methylamino-4-phenyl-butyl)-amide hydrochloride (250 mg, 0.61 mmol), 1-methyl-1 H-indole-4-carboxylic acid (128 mg, 0.73 mmol), HOBt (112 mg, 0.73 mmol), EDC x HCI (176 mg, 0.92 mmol), and triethylamine (0.34 ml, 2.4 mmol) were dissolved in DCM (10 ml) and the reaction was stirred at rt over night. The mixture was diluted with EtOAc, washed with NaHC03- and NaCI-soln., dried (Na2S0 ), filtered and concentrated. The crude product was purified by chromatography (Flashmaster, heptane to EtOAc over 25 min; EtOAc for 10 min) to yield 191 mg (63%) of the title compound as off-white solid. [1 H-NMR (DMSO, 600 MHz, rotamers) 9.06/8.82 (br s, 1 H), 7.74-7.67 (m, 2H), 7.42-6.25 (m, 11H), 6.11/5.63 (s, 1H), 5.14/3.65 (br s, 1 H), 4.13/4.00 (s, 3H), 3.75/3.59 (s, 3H), 3.49-3.22 (m, 2H), 3.04/2.59 (s, 3H), 3.00-2.80 (m, 2H), 1.99-1.53 (m, 2H); LCMS RtA = 3.136 min; [M+H]+ = 494.2]., 90924-06-4

The synthetic route of 90924-06-4 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; NOVARTIS AG; BETSCHART, Claudia; COTESTA, Simona; HINTERMANN, Samuel; WAGNER, Juergen; ROY, Bernard, Lucien; GERSPACHER, Marc; VON MATT, Anette; BEHNKE, Dirk; WO2011/73316; (2011); 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.676273-39-5,3-Iodo-1-tosyl-1H-indole-5-carbonitrile,as a common compound, the synthetic route is as follows.

676273-39-5, Example 44 Preparation of QR-0311[00400] Compound QR-031 1 was prepared by reactions depicted in Scheme 50 below.[00401] The following General Procedure H was used. General Procedure H[00402] Arylbromide or aryliodide (1 mmol). boric acid ( 1.2 mmol) andPd(OAc)2 (0.05 mmol) in DMF (5 niL) were stirred under argon at 60-90 0C for 5-16 h. The mixture was then cooled to room temperature, ethyl acetate (50 mL) was added and the mixture washed with brine 3 times (50 mL). The organic layer wasdried with MgSO4 and concentrated. The residue was purified by flash columnchromatography.100403] General Procedure H was used to yield 259 (63% yield). 1H NMR(CDCl3): 2.38 (s, 3H). 7.30 (d, 2H. J=8.4). 7.37-7.41 (m, 2H), 7.55 (s, I H), 7.64 (d.1 H. J=8.6), 7.82-8-7.86 (m, 4H), 7.96 (s. 1 H), 8.14 (d. 1 H, .1=8.6). 8.31 (s, 1 H).

676273-39-5 3-Iodo-1-tosyl-1H-indole-5-carbonitrile 21955913, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; QUEEN’S UNIVERSITY AT KINGSTON; WO2008/58402; (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

10601-19-1, 5-Methoxy-1H-indole-3-carbaldehyde is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

5-methoxy-indole 22 (1.78 g, 9.40 mmol) was added gradually and under dry argon to a suspension of NaH (0.564 g of a 60% dispersion, 14.11 mmol) in dry DMF (4 mL). The suspension was stirred at room temperature for 10 min and cooled to 0 C, and MeI (0.81 g, 5.71 mmol) was added over 5 min. The solution was then heated at 40 C for 30 min, cooled, poured into cold water. The mixture was extracted with EtOAc (2× 150 mL), dried and evaporated. The residue was used without purification (1.03 g, 95%). 1H NMR (300 MHz, DMSO-d6): delta (ppm) 9.72 (s, 1H), 8.45 (s, 1H), 7.82 (d, J = 9.1 Hz, 1H), 7.37 (d, J = 9.1 Hz, 1H), 3.93 (s, 3H), 3.91 (s, 3H); MS (ESI) m/z: 190.1 [M+H]+.

10601-19-1, The synthetic route of 10601-19-1 has been constantly updated, and we look forward to future research findings.

Reference：
Article; Xu, Shengtao; Yao, Hong; Pei, Lingling; Hu, Mei; Li, Dahong; Qiu, Yangyi; Wang, Guangyu; Wu, Liang; Yao, Hequan; Zhu, Zheying; Xu, Jinyi; European Journal of Medicinal Chemistry; vol. 132; (2017); p. 310 – 321;,
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

59908-47-3, 5-Chloro-1-methyl-1H-indole-2-carboxylic acid is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,59908-47-3

Production Example 5-4tert-butyl 6-{[5-chloro-1-methyl-1H-indol-2-yl]carbonyl}amino)octahydroisoquinoline-2(1H)-carboxylate To a methanol solution (100 mL) of the compound obtained in Production example 5-3 (3.3 g), 10% palladium carbon (500 mg) was added, and the resulting solution was stirred overnight at room temperature under 1 atm hydrogen atmosphere. The reaction solution was filtered and the filtrate was concentrated under reduced pressure. To a DMF (70 mL) solution of the residue, commercially available 5-chloro-1-methyl-1H-indole-2-carboxylic acid (2.4 g), HATU (4.4 g) and subsequently diisopropylethylamine (4.1 mL) were added, and the resulting solution was stirred overnight at room temperature. Water was added to the reaction solution, and the solution was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1 to 1:2), whereby the title compound (3.2 g) was obtained as a single optically active isomer (the arrangement in the structural formula is a relative configuration).

As the paragraph descriping shows that 59908-47-3 is playing an increasingly important role.

Reference：
Patent; MSD K.K; US2012/28990; (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.2795-41-7,6-Fluoroindole-3-carboxaldehyde,as a common compound, the synthetic route is as follows.

General procedure: Piperidine (0.08 mL) was added to methanol (25 mL) dissolved in substituted aldehydes 5-7 (0.18 mmol) and starting 2-indolinone derivatives 8-11 (0.18 mmol) which were prepared as described previously refPreviewPlaceHolder[6], refPreviewPlaceHolder[21], refPreviewPlaceHolder[22], refPreviewPlaceHolder[23], refPreviewPlaceHolder[24] and refPreviewPlaceHolder[25]. The mixture was refluxed for 5 h. For the targeted compounds 12-21 and 28-36, the mixture was evaporated to remove the solvent and the residue was purified by column chromatography (CH2Cl2/MeOH 100:1-10:1). For the targeted compounds 22-27, ethyl ether (15 mL) was added to the residue and the yellow precipitate was collected by filtration. The obtained precipitate was subjected to the hydrogen chloride saturated methanol to afford it as hydrochloride derivative. All the targeted compounds 12-36 show moderate to good yields under this reaction condition with the yields of 60-92%.

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

Reference：
Article; Zou, Hongbin; Zhang, Liang; Ouyang, Jingfeng; Giulianotti, Marc A.; Yu, Yongping; European Journal of Medicinal Chemistry; vol. 46; 12; (2011); p. 5970 – 5977;,
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.343-90-8,1-(5-Fluoro-1H-indol-3-yl)-N,N-dimethylmethanamine,as a common compound, the synthetic route is as follows.

General procedure: To a solution of gramine[1] (8.00 mmol) and AcOH (114 muL, 2.00 mmol) in THF (10 mL) a solution of dimethylsulphate (3.79 mL, 40 mmol) and AcOH (114 muL, 2.00 mmol) in THF (8 mL) was added at 0 C dropwise. After stirringfor 1 h, Et2O (40 ml) was added and the reaction mixture was cooled to -18 C, precipitates were filtered, washed with Et2O (3*30 mL), dried over P2O5 in vacuum to afford gramine methosulfate derivative., 343-90-8

Big data shows that 343-90-8 is playing an increasingly important role.

Reference：
Article; Reinfelds, Matiss; Kalinins, Konstantins; Katkevica, Dace; Zemribo, Ronalds; Katkevics, Martins; Tetrahedron Letters; vol. 56; 43; (2015); p. 5882 – 5885;,
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

In a 250 mL flask was placed terf-butyl 5-(benzyloxy)-1H-indole-1-carboxylate (3.3g, 14 mmol) in 100 mL of acetone. 1,3-Dibromopropane (5.74 mL, 56.6 mmol) wasadded, followed by cesium carbonate (5.5 g, 17 mmol). The reaction was heated toreflux for 5 h. The reaction was cooled to room temperature and diluted with water (200mL). The mixture was transferred to a separatory funnel and extracted with ethyl acetate(2 x 150 mL). The combined organics were dried (MgSO4), filtered, and evaporated.The residue was then purified via flash chromatography to provide 4.7 g of terf-butyl 5-(3-bromopropoxy)-1H-indole-1-carboxylate (94%). 1H-NMR (DMSO-d6) 5 7.99-7.89 (d, 1H),7.61 (s, 1H), 7.17 (s, 1H), 6.98-6.91, (d, 1H), 6.62 (s, 1H), 4.16-4.05 (t, 2H), 3.64 (t, 2H),2.37-2.20 (m, 2H). LCMS RT= 3.55 min; [M]+= 254.1.

434958-85-7, As the paragraph descriping shows that 434958-85-7 is playing an increasingly important role.

Reference：
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2005/51957; (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