Month: March 2022

923197-75-5, (6-Bromo-1H-indol-2-yl)methanol is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

923197-75-5, General procedure: To a stirred solution of the crude (1H-indol-2-yl)methanol (1.07 g, 7.3 mmol) in anhydrous CH2Cl2(10 mL) at coldbath temperature (~10 .) was added portionwise pyridinium chlorochromate (PCC) (1.89 g, 8.1mmol). Reaction was stirred at ambient temperature for 2 hours. Reaction was diluted with CH2Cl2 and filteredthrough a pad of celite and washed with CH2Cl2. After evaporation of solvent, crude product was silica-columnchromatographed (Biotage) using Acetone: Hexane as an eluent to yield 1H-indole-2-carbaldehyde (2d) (0.43 g,41% yield).

923197-75-5 (6-Bromo-1H-indol-2-yl)methanol 13567957, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Article; Jiang, Zeng-Qiang; Miao, Da-Zhuang; Tong, Yao; Pan, Qiang; Li, Xiao-Tong; Hu, Ren-He; Han, Shi-Qing; Synthesis; vol. 47; 13; (2015); p. 1913 – 1921;,
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

1059630-08-8, (4aS,9bR)-Ethyl 6-bromo-3,4,4a,5-tetrahydro-1H-pyrido[4,3-b]indole-2(9bH)-carboxylate is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 1 : To a degassed mixture of (4aS,9bR)-ethyl 6-bromo-3,4,4a,5-tetrahydro- lH-pyrido[4,3-b]indole-2(9bH)-carboxylate (1.60 g, 8.0 mmol), 2-chloro-2,2-di- deuteri oacetam i de (2.5 g, 26 mmol), and KI (2.68 g, l6mmol) in dioxane (30 mL), diisopropylethylamine (3.0 mL, 16 mmol) is added at room temperature. The reaction mixture is then heated to 104 C under vigorous stirring for 5 days. Solvents are removed under vacuum and the residue is suspended in dichloromethane (50 mL) and extracted with water (20 mL). The organic phase is separated, dried over anhydrous K2CO3 and (0280) concentrated to a residue. The product is purified by silica gel column chromatography using a gradient of 0 – 100% ethyl acetate in hexanes to obtain (4aS,9bR)-ethyl 5-(2-amino- 1 , 1 -di- 2-oxoethyl)-6-bromo-3,4,4a,5-tetrahydro-lH-pyrido[4,3-b]indole-2(9bH)-carboxylate as a brown oil (1.26 g, yield 41%). MS (ESI) m/z 384.1 [M+l]. The synthesis of the starting material is disclosed in US 2010/113781. The reaction scheme is shown below:

1059630-08-8, The synthetic route of 1059630-08-8 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; INTRA-CELLULAR THERAPIES, INC.; LI, Peng; ZHANG, Qiang; DAVIS, Robert; (63 pag.)WO2019/183341; (2019); 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

289483-82-5, 4-Methyl-7-nitro-1H-indole-3-carbonitrile is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

PRODUCTION EXAMPLE 12 7-Amino-3-cyano-4-methyl-1H-indole 12.6 g (62.6 mmol) of the compound of Production Example 6 was dissolved in a mixed solution of 100 ml of tetrahydrofuran and 100 ml of methanol, and the mixture was hydrogenated at an ordinary temperature under 3 atoms in the presence of 430 mg (1.87 mmol) of platinum oxide. The catalyst was filtered off and the filtrate was concentrated to dryness. Then, a mixed solution of tert-butyl methyl ether and hexane was added to the residue and the crystals were collected by filtration, to give 10.7 g of the title compound. 50.5 g (186 mmol) of the compound of Production Example 11 was dissolved in 400 ml of dichloromethane. In nitrogen atmosphere, 210 ml (2.76 mol) of trifluoroacetic acid was added thereto at 0 C., followed by stirring at room temperature for 40 minutes. The reaction mixture was adjusted to pH 7 by adding a 5N aqueous sodium hydroxide thereto. The solvent was removed, and then the residue was extracted with ethyl acetate. The organic layer was successively washed with water and brine, dried over magnesium sulfate and concentrated to dryness. A mixed solution of diethyl ether and hexane was added to the residue and the crystals were collected by filtration, to give 24.5 g of the title compound. 1H-NMR(DMSO-d6) delta (ppm): 2.47(3H, s), 5.07(2H, s), 6.34(1H, d, J=7.6 Hz), 6.64(1H, d, J=7.6 Hz), 8.10(1H, s), 11.70(1H, br s)

289483-82-5, As the paragraph descriping shows that 289483-82-5 is playing an increasingly important role.

Reference：
Patent; Wakabayashi, Toshiaki; Funahashi, Yasuhiro; Hata, Naoko; Semba, Taro; Yamamoto, Yuji; Haneda, Toru; Owa, Takashi; Tsuruoka, Akihiko; Kamata, Junichi; Okabe, Tadashi; Takahashi, Keiko; Nara, Kazumasa; Hamaoka, Shinichi; Ueda, Norihiro; US2004/18192; (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

676273-39-5, 3-Iodo-1-tosyl-1H-indole-5-carbonitrile is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

676273-39-5, Compound 15 (10 g), Thiophene boronic acid and K2CO3 were taken in Dioxane (120 ml): Wa- ter(15ml) mixture in a two neck RB flask equipped with Nitrogen balloon and reflux condenser. Reaction mass was degassed for 20 min. Palladium catalyst was added and reaction mass was again degassed for 3 min. Reaction mixture was refluxed at 110C for 2 hrs under Nitrogen. Re- action progress was monitor by TLC. After completion of the reaction, the mixture was filtered through a bed of celite. Filtrate was diluted with ethyl acetate. Ethyl acetate layer was washed with water and brine and concentrated. Crude material was taken in 80 ml methanol and stirred for 45 min at RT. Solid obtained is filtered and wash with cold methanol to get 8.4 g white solid product. (0863) 1H NMR (300 MHz, DMSO-d6) delta 8.50 (s, 1H), 8.40 (s, 1H), 8.22- 8.08 (m, 2H), 7.98 (d, J = 8.3 Hz, 2H), 7.82 (d, J = 8.7 Hz, 1H), 7.70 (d, J = 1.8 Hz, 2H), 7.41 (d, J = 8.2 Hz, 2H), 2.31 (s, 3H).

The synthetic route of 676273-39-5 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; BASF SE; POONOTH, Manojkumar; RHEINHEIMER, Joachim; RATH, Rakesh; ROSENBAUM, Claudia; WIEBE, Christine; BRAHM, Lutz; RUDOLF, Georg Christoph; KHANNA, Smriti; HADEN, Egon; ROEHL, Franz; SIEPE, Isabella; KREMZOW-GRAW, Doris; SCHIFFER, Helmut; (199 pag.)WO2018/210659; (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.171879-99-5,4-Chloro-6-methyl-7-azaindole,as a common compound, the synthetic route is as follows.

A mixture of 4-chloro-6-methyl-1 H-pyrrolo[2,3-b]pyridine (47mg, 0.291 mmol), 3-(4,4,5,5- tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyrazolo[1 ,5-b]pyridazine (107mg, 0.436mmol), X Phos Pd G3 (19.6mg, 0.023mmol) and potassium phosphate (124mg, 0.582mmol) in degassed ethanol (3.0ml_) and water (1.5ml_) was heated at 140C for 30 mins in the microwave. After cooling it was partitioned between ethyl acetate and water and the organic layer was separated, washed with brine, dried (Na2S04) and concentrated in vacuo. The crude product was purified by MDAP (Basic) to afford the title compound as a glass (27mg, 37%) LCMS (Method 1): Rt 2.12 min, m/z 249.8 [MH+]. 1 H NMR (400 MHz, d6-DMSO): 2.59 (3H, s), 6.56 (1 H, d, J=3.5 Hz), 7.19 (1 H, s), 7.34 (1 H, dd, J=4.4, 9.1 Hz), 7.43 (1 H, d, J=3.5 Hz), 8.48 (1 H, dd, J=1.8, 9.2 Hz), 8.56- 8.58 (2H, m), 11.59 (1 H, s), 171879-99-5

The synthetic route of 171879-99-5 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; THE UNIVERSITY OF NOTTINGHAM; BROOK, David; HAYES, Chris; BENNETT, Nicholas; PALFRAMAN, Matthew; CRAMP, Sue; BULL, Richard; BODNARCHUK, Michael; (262 pag.)WO2019/58132; (2019); 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.31241-19-7,5-Methoxy-2,3,3-trimethyl-3H-indole,as a common compound, the synthetic route is as follows.

5-Methoxy-2,3,3-trimethyl-3H-indole (2 g, 10.6 mmol) and 1-bromobutane (4.3 g, 31.7 mmol) were dissolved in 60 mL acetonitrile and warmed to 75 C The reaction was refluxed for 50 h. After the reaction was completed, it was filtered to give a brown oily liquid (2.1 g,Yield 61.0%,After purification by column chromatography, 2-2 1.5 g of pale yellow solid was obtained.

31241-19-7, As the paragraph descriping shows that 31241-19-7 is playing an increasingly important role.

Reference：
Patent; Shenyang Pharmaceutical University; Wang Dun; Wang Yongjun; Yang Xiaoguang; Lv Qingzhi; (25 pag.)CN108752319; (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

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.

A mixture of 2,2,2-trifluro-1 H-indol-3-yl)ethanone (0.55 g, 2.58 mmol), K2CO3 (0.43 g, 3.1 1 mmol) and propyrgyl bromide (2 ml) was stirred in anhydrous DMF (8 ml) for 4 h. The mixture was quenched with aqueous NH4CI and diluted to 50 ml with EtOAc. The organic layer was separated, washed with w H2O, dried over MgSO4 and filtered. The filtrate was evaporated to dryness to give the product (0.57 g; 87%), as yellow solid. 1 H-NMR (CDCI3) 2.58 (tr, 1 H, J = 2.55 Hz); 4.96 (d, 2H, J = 2.55 Hz); 7.48 – 7.31 (m, 3H); 7.99 (s, 1 H); 8.41 – 8.38 (m, 1 H)., 14618-45-2

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

Reference：
Patent; AKAAL PHARMA PTY LTD; GILL, Gurmit, S.; GROBELNY, Damian, W.; WO2010/42998; (2010); 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

53924-05-3, 7-Chloroindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

53924-05-3, Example 16 Procedure Used for the Preparation of 1-4. Exemplified for the Preparation of 6-chloroindole-3-carboxaldehyde (1) Phosphorus oxychloride (0.66 mL, 7 mmol) was added dropwise to anhydrous DMF (5 mL) at 0 C. under argon. A solution of 7-chloroindole (1 g, 6.6 mmol) in anhydrous DMF (15 mL) was added dropwise at room temperature and the resulting mixture was stirred for 2 h. The reaction mixture was poured into ice and saturated NaHCO3 and extracted with ethyl acetate. The combined organic solutions were washed with saturated NaCl (10 mL*3), dried over anhydrous MgSO4, filtered and concentrated to give 990 mg of product, 1, as a yellow-orange solid (83%).

53924-05-3 7-Chloroindole 104644, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; Brigham and Women’s Hospital, Inc.; President and Fellows of Harvard College; US2005/119260; (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

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

The title compound can also be prepared according to the following procedure: TMSOTf (1.4 ml_, 7.7 mmol) was added dropwise to a solution of tetrahydro-4H-thiopyran- 4-one (0.88 g, 7.6 mmol) in DCM (80 ml.) in the presence of molecular sieves at 0 0C (bath temp). A solution of ethyl 5-bromo-1 /-/-indole-7-carboxylate (2 g, 7.4 mmol). in DCM (20 ml.) was added and the reaction was stirred for 15 min. Triethylsilane (2 ml_, 12.5 mmol) was added and the reaction was allowed to warm to room temperature overnight. Saturated aqueous Na2CO3 was added, the layers separated and the aqueous layer extracted with DCM. The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure. The residue was washed with MeOH and dried in a vacuum oven, giving 2.07 g (76%) of the title compound., 1065181-58-9

As the paragraph descriping shows that 1065181-58-9 is playing an increasingly important role.

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

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

Indole amide (1d) (2.09 g, 12 mmol) and 5-bromopyrimidine (2.48 g, 15.6 [MMOL)] were dissolved in DMF (12 mL), and potassium carbonate (1.82 g, 13.2 [MMOL)] and [CUO] (477 mg, 6.0 [MMOL)] were added and the reaction was stirred at 165 [C] for 18 h. The volatiles were removed under vacuo and the residue was partitioned between [CHC13] (300 mL) and water (150 mL). Two layers were separated and the aqueous layer was extracted with [CHC13] (100 mL). The combined organic layers were washed with water, brine and then filtered through Celite to remove insolubles. The filtrate was evaporated under vacuo to ca. 30 mL of volume, to which were added EtOAc (50 mL) and hexane (20 mL). The mixture was cooled to 0 [C,] and the resulting solid was collected by filtration to give 1.30 g of Compound 4a as a light yellow [SOLID.’H] NMR (CD30D) 8 9.13 (s, 1 H), 9.10 (s, 2 H), 7.69 (d, J = 8.0 Hz, 1 H), 7.60 (d, J = 8.2 Hz, 1 H), 7.53 (s, 1 H), 7.30-7. 22 (m, 2 H), 3.74 (s, 2 H). ES-MS m/z 253 [(MH+).] The a-keto ester 1c (78 mg, 0.28 [MMOL)] and amide Compound 4a (50 g, 0.2 [MMOL)] were combined in dry THF (3 mL) under argon and cooled in an ice bath as 1 M potassium t-butoxid in THF (0.8 mL, 0.8 [MMOL)] was added dropwise. The reaction mixture was stirred at 0 [C] for 40 min, then rt for 80 min. The mixture was cooled back to 0 [C] while 12 N [HCI] (1 mL) was slowly added. After stirred at rt for 5 min, the mixture was diluted with H20 (5 mL), basified with 3N [NAOH,] and extracted with EtOAc. The organic layers were combined and washed with brine, dried [(NA2SO4)] and evaporated in vacuo to give a crude solid. The crude product was purified by reverse-phase HPLC using a gradient of 10% to 90% [ACETONITRILE/WATER] (containing 0.2% TFA) to afford Compound 11 (32 mg) as a red-orange solid (TFA [SALT).’H] NMR (DMSO-d6) [8] 9.26 (s, 1 H), 9.07 (s, 2 H), 8.74 (s, 1 H), 8.66 (d, J = 3.6 Hz, [1] H), 8.14 (s, 1 H), 8.08 (m, 1 H), 8.05 (s, 1 H), 7.66 (dd, [J = 4.] 7,8. 2 Hz, 1 H), 7.61 (d, [J =] 8.3 Hz, 1 H), 7.53 (d, J = 8.3 Hz, [1] H), 7.20 (m, 2 H), 7.12 (s, 1 H), 7.09 (s, [1H),] 6.96 (m, 2H). ES-MS m/z 483 (MH+).

879-37-8 Indole-3-acetamide 397, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; Janssen Pharmaceutica N.V.; WO2003/104222; (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