Month: March 2022

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

The mixture of ethyl 7-bromo-1H-indole-2-carboxylate (536 mg, 2 mmol), (4- fluorophenyl)boronic acid (420 mg, 3 mmol) in a mixture of toluene, ethanol and sat. NaHCO3 solution (10/4/4 mL) was degassed and Pd(PPh3)4 (100 mg, 0.09 mmol) was added. The reaction mixture was heated at 100 oC overnight and extracted with EtOAc, then washed with brine and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel to give the desired product (320 mg, 57% yield) as an off-white powder. 1H NMR (300 MHz, CDCl3) delta 8.89 (br, 1H), 7.69 (d, J = 8.4 Hz, 1H), 7.60 (m, 1H), 7.58 (m, 1H), 7.23 (m, 5H), 4.40 (q, J = 6.9 Hz, 2H), 1.41 (t, J = 6.9 Hz, 3H).

16732-69-7, As the paragraph descriping shows that 16732-69-7 is playing an increasingly important role.

Reference：
Patent; LAVOIE, Edmond J.; PARHI, Ajit; YUAN, Yi; ZHANG, Yongzheng; SUN, Yangsheng; RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY; TAXIS PHARMACEUTICALS, INC.; (251 pag.)WO2018/165611; (2018); 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.900514-08-1,5-Chloro-3-iodo-7-azaindole,as a common compound, the synthetic route is as follows.

900514-08-1, Step 2: Preparation of 5-chloro-3-iodo-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine 5-chloro-3-iodo-1H-pyrrolo[2,3-b]pyridine (1.25 g, 4.5 mmol) was dissolved in dry tetrahydrofuran (26 mL), and 60% sodium hydride (270 mg, 6.75 mmol) was added in batches under an ice bath and under a nitrogen atmosphere. The reaction solution was stirred for 15 min under a liquid ice bath, then chlorotriisopropylsilane (1.25 mL, 5.9 mmol) was added dropwise. The reaction solution was warmed to room temperature, then stirred for 2 hrs, quenched with a saturated ammonium chloride aqueous solution, and extracted with ethyl acetate. The organic phase was dried, concentrated and then separated by column chromatography [eluent: petroleum ether] to obtain 5-chloro-3-iodo-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine (1.75 g, yield 90%).

As the paragraph descriping shows that 900514-08-1 is playing an increasingly important role.

Reference：
Patent; Abbisko Therapeutics Co., Ltd.; ZHANG, Mingming; ZHAO, Baowei; YU, Hongping; CHEN, Zhui; XU, Yaochang; (58 pag.)US2020/140431; (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

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.14618-45-2,3-(Trifluoroacetyl)indole,as a common compound, the synthetic route is as follows.

To a solution of 2,2,2-trifluoro-l-(lH-indol-3-yl)ethanone (0.20 g, 0.938 mmol) in THF (1 mL) in an ice-bath was added sodium borohydride (71.00 mg, 1.877 mmol) under N2. Then boron trifluoride diethyl ether (0.357 mL, 2.815 mmol) was added dropwise. The reaction was let stirred for 2 h while warmed to room temperature. The mixture was poured into a mixture of ice-water and 5% aqueous NaHC03and extracted with ethyl acetate. The combined organics were concentrated. The residue was purified by silica gel column chromatography to give the title compound (90 mg). LCMS m/z = 200.4 [M+H]+; NMR (400 MHz, CD3OD) delta ppm 3.57 (q, J = 11.1 Hz, 2H), 7.04 (t, J = 7.4 Hz, 1H), 7.12 (t, J = 7.3 Hz, 1H), 7.20 (s, 1H), 7.37 (d, J = 8.0 Hz, 1H), 7.54 (d, J = 7.9 Hz, 1H).

14618-45-2, 14618-45-2 3-(Trifluoroacetyl)indole 589126, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; ARENA PHARMACEUTICALS, INC.; SEMPLE, Graeme; BEHAN, Dominic P.; FEICHTINGER, Konrad; GLICKLICH, Alan; GROTTICK, Andrew J.; KAM, Maria Matilde Sanchez; KASEM, Michelle; LEHMANN, Juerg; REN, Albert S.; SCHRADER, Thomas O.; SHANAHAN, William R.; WONG, Amy Siu-Ting; ZHU, Xiuwen; WO2015/66344; (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

14618-45-2, 3-(Trifluoroacetyl)indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of this compound (11 g, 50 mmol) in 100 mL acetone were added MeI (10 mL, 150 mmol) and potassium carbonate (18 g), and stirring was continued at RT for 2 h. Acetone was removed in vacuo. Water and methylene chloride were added to the residue. The organic layer was separated, washed with brine, dried and concentrated in vacuo to yield crude 1-methyl-3-trifluoroacetyl-1H-indole., 14618-45-2

As the paragraph descriping shows that 14618-45-2 is playing an increasingly important role.

Reference：
Patent; Monsanto Company; US5994270; (1999); 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

192189-07-4, tert-Butyl 3-iodo-1H-indole-1-carboxylate is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,192189-07-4

In a 100 mL round bottom flask, N-Boc-3-iodoindole (0.65 g, 1.45 mmol),Tetrakis (triphenylphosphine) palladium (0.1g, 0.04mmol) was dissolved in 10mL of 1,4-dioxane,Replace gas. Triethylamine (2 mL, 14.5 mmol) and pinacol borane (0.3 mL, 2.2 mmol) were added with a syringe, and the mixture was stirred at 80 C after the dropwise addition. Stop heating after 3h,After cooling to room temperature, Ia-1 (0.58 g, 1.45 mmol) was added to the system under the protection of argon.Cesium carbonate (2.4 g, 7.25 mmol), 12 mL of methanol. After the addition was complete, the system was stirred at 100 C. overnight and monitored by TLC. After the reaction is completed, spin column chromatography is directly performed (V dichloromethane: V methanol = 100: 1 ? V dichloromethane: V methanol = 20: 1),The crude product was directly dissolved in 20 mL of acetonitrile, Boc2O (0.62 mL, 2.7 mmol) was added thereto, DMAP (0.1 g, 0.3 mmol) was stirred at room temperature for 2 h, and TLC was monitored.After the reaction was completed, spin column chromatography was performed directly (V petroleum ether: V ethyl acetate = 100: 1 ? V petroleum ether alkane: V ethyl acetate = 10: 1) to obtain 0.2 g of a white solid with a yield of 30%.

The synthetic route of 192189-07-4 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Nankai University; Wang Qingmin; Liu Yuxiu; Dong Ji; Wang Ziwen; Song Hongjian; Li Yongqiang; (22 pag.)CN110759893; (2020); 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

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

53462-88-7, Methyl 3-formyl-1H-indole-4-carboxylate is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

53462-88-7, A) 2.1 g of 80% pure sodium hydride were added in portions to a solution of 7 g of methyl 3-formylindole-4-carboxylate (see Example 1A for preparation) in 250 ml of dry dimethylformamide at room temperature under a nitrogen atmosphere. The reaction mixture was stirred at 50 C. for 1 hour. Subsequently, 7 ml of methyl iodide was added through a dropping funnel, and the reaction mixture was stirred at 50 C. for a further 2 hours. To work up the reaction mixture it was evaporated to dryness under reduced pressure and taken up in a mixture of 50 ml of water and 50 ml of dichloromethane. The dichloromethane phase was separated, and the aqueous phase was extracted once more with 50 ml of dichloromethane. The organic phases were combined, dried over sodium sulfate, filtered and evaporated. The remaining crystalline crude product was recrystallized from diethyl ether. Drying of the crystals resulted in 6.9 g of methyl 1-methyl-3-formylindole-4-carboxylate with a melting point of 128-129 C.

The synthetic route of 53462-88-7 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Kali-Chemie Pharma GmbH; US5272143; (1993); 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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.101861-63-6,4,6-Dichloroindole-2-carboxylic acid,as a common compound, the synthetic route is as follows.

In the reaction bottle,22 g of 4,6-dichloroindolecarboxylic acid was added to 150 mL of DMSO, and then 3 g of copper chloride was added.The reaction was heated at 120 C for 1 h,TLC monitors the reaction of the starting material completely, and the reaction solution is filtered, and then 200 mL of dichloromethane is added to extract the reaction solution three times.The organic phases were combined, washed with 200 mL of water and concentrated.Then in a mixture of acetone and n-hexane (V acetone: V-hexane = 3:1)Recrystallization from 100 mL gives 4,6-dichloroanthracene 14g, 101861-63-6

As the paragraph descriping shows that 101861-63-6 is playing an increasingly important role.

Reference：
Patent; Henan Normal University; Xu Guiqing; Wang Jiahao; Ren Baoqi; Zhou Yingjie; Mao Longfei; (9 pag.)CN109160895; (2019); 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

90924-06-4, 1-Methyl-4-indolecarboxylic Acid is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,90924-06-4

To a solution of 4-METHYL-4- [ (3S)-3-METHYL-4- [ (1 R)-1- [4- (TRIFLUOROMETHYL) PHENYL] ETHYL] PIPERAZIN-1-YL]-1-PIPERIDINECARBOXYLIC ACID-DIMETHYLETHYL ester (127 mg, 0.27 MMOL) in CH2CI2 (3 mL) was added trifluoromethyl acetic acid (1.5 mL) at room temperature. After 2h the reaction mixture was concentrated in vacuo, and dried under vacuum for 3 h. Re-dissolved the product in DMF (5 mL), then 1-methyl-1 H-indol-4-carboxylic acid (52 mg, 0.30 MMOL), Et3N (55 mg, 0.54 MMOL), and HATU (134 mg, 0.35 MMOL) was added successively at room temperature. After 16 h the reaction mixture was poured into ice water (10 mL), and the mixture was extracted with EtOAc (3X20 mL). The organic phase was washed with NAHCO3 (10 mL, sat. ) and brine (10 mL), and dried over NA2SO4. Concentration in vacuo, and purification by column chromatography (CH2CI2-MEOH, 9: 1) afforded the title compound as a yellow solid. MS: 526 (M+).’H NMR (CDCl3, 400MHZ) : S : 0.9 (s, 3H), 1.14 (d, 3H), 1.3 (d, 4H), 1.4-1. 8 (m, 2H), 1.82-2. 05 (m, 1H), 2.18-2. 8 (m, 6H), 2.9-3. 1 (m, 1H), 3.1-3. 3 (m, 1H), 3.3-3. 7 (m, 2H), 3.8 (s, 3H), 3.9-4. 3 (m, 2H), 6.48 (m, 1H), 7.05-7. 16 (m, 2H), 7. 18-7. 28 (M, 1 H), 7.3-7. 38 (m, 1 H), 7.46-7. 6 (m, 4H).

As the paragraph descriping shows that 90924-06-4 is playing an increasingly important role.

Reference：
Patent; SCHERING AKTIENGESELLSCHAFT; WO2004/113323; (2004); 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