Day: March 16, 2022

101861-63-6, 4,6-Dichloroindole-2-carboxylic acid is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example IPreparation of 4, 6-dichloro-N-(4, 4-dimeth ylcyclohexyl)- IH-indole-2-carboxamide (IA): (1A)A mixture of 4,6-dichloro-1 H-indole-2-carboxylic acid -1d: 205 g, 891 .1 mmol in 9 batches) and 4,4-dimethylcyclohexylamine.HCI -6b: 160.4 g, 980.2 mmol) in dry DMF (2290 mL) was cooled to 000 and added HATU (406.3 g, 1070 mmol) followed by5 DIPEA (775.5 mL, 4450 mmol) drop-wise and the mixture was stirred under inert atmosphere at room temperature for 17 h. Ice-cold water (7000 mL) was added to the reaction mixture and stirred vigorously and the precipitated solid was collected by filtration and dried thoroughly. The combined crude solids from all batches were purified by column chromatography over silica gel (100-200 mesh) using a solvent gradient of10 30%-40% ethyl acetate in hexanes as eluentto afford 213 g of light brown solid. It was triturated with ether/hexanes (3:7) in five cycles to give off-white solid. The solid was treated with charcoal in ethyl acetate/methanol (4:1) at 70C for 3h and filtered to afford 207 g (68.5%) of 4,6-dichloro-N-(4,4-dimethylcyclohexyl)-1 H-indole-2-carboxamide (IA) as a white solid.15 NMR (400 MHz, DMSO-d6): 6 12.06 (5, 1 H), 8.44 (d, J = 8.0 Hz, 1 H), 7.41 (5,1 H), 7.30 (5, 1 H), 7.22 (5, 1 H), 3.80-3.65 (m, 1 H), 1 .70-1 .60 (m, 2H), 1.60-1 .45 (m, 2H),1.45-1.35 (m, 2H), 1.35-1.20 (m, 2H), 0.95 (5, 3H), 0.93 (5, 3H). 130 NMR (100 MHz,DMSO-d6): 6159.3, 136.7, 133.7, 127.5, 126.2, 124.8, 119.3, 111.1, 100.6, 48.1, 37.6(20), 32.1, 29.3 (20), 28.1 (20). ESI MS: m/z 339.01 [(Mi-H] & 341 .03 [(M+2)+H]. HPLC 20 purity: 99.7%.

101861-63-6, The synthetic route of 101861-63-6 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; NOVARTIS AG; JIRICEK, Jan; KONDREDDI, Ravinder Reddy; SMITH, Paul William; WO2014/37900; (2014); 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

1469-48-3, cis-3a,4,7,7a-Tetrahydro-1H-isoindole-1,3(2H)-dione is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

a Cis-Octahydroisoindole Cis-4-cyclohexene-1,2-dicarboximide (10.9 g) was hydrogenated over 10% palladium on carbon (1 g) in absolute ethanol (420 ml) at 50 psi for 10 minutes. The mixture was filtered then evaporated to give cis-cyclohexane-1,2-dicarboximide (10.6 g). To anhydrous diethyl ether (200 ml) was cannulated under nitrogen a 1M diethyl ether solution (200 ml) of lithium aluminium hydride.

1469-48-3, As the paragraph descriping shows that 1469-48-3 is playing an increasingly important role.

Reference：
Patent; Merck Sharp & Dohme, Ltd.; US5618812; (1997); 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

393553-57-6, 6-Bromo-4-methoxy-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,393553-57-6

A solution of 6-bromo-4-methoxyindole (1, 100mg, 0.44mmol) and N-(2,2-dimethoxyethyl)-trifluoroacetamide16 (178mg, 0.88mmol, 2.0 equiv) in dichloromethane (3.0mL) was added to a solution of triethylsilane (0.43mL, 2.64mmol, 6 equiv) and TFA (0.17mL, 2.21mmol, 5 equiv) in dichloromethane (2.0mL). The reaction mixture was stirred at room temperature for 3h, cooled down to 0C and then neutralized with a saturated solution of sodium bicarbonate (?75mL). The aqueous phase was extracted with dichloromethane (3×50mL) and the combined organic phases washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. Purification by column chromatography on silica gel eluting with ethyl acetate-petroleum ether (1:3) gave the title compound (83mg, 0.23mmol, 51%) as light yellow solid, M.p. 111.3-113.1C; HRMS [ESI, (M+Na)+] found 386.9925; [C13H1279BrF3N2O2+Na]+ requires 386.9926; numax (neat)/cm-1 3434, 3343, 2938, 2885, 1690, 1615, 1175, 978, 795; deltaH (500MHz, CDCl3) 8.07 (1H, br s, NH), 7.17 (1H, d, J 1.4, CH), 6.96 (1H, br s, NH), 6.89 (1H, d, J 2.3, CH), 6.65 (1H, d, J 1.4, CH), 3.94 (3H, s, Me), 3.62 (2H, dd, J 12.0, 5.7, CH2), 3.12 (2H, dd, J 9.3, 3.4, CH2); deltaC (100MHz, CDCl3) 154.2 (C=O), 138.5 (C), 122.0 (CH), 116.12 (C), 116.10 (C), 113.1 (C), 108.3 (CH), 104.3 (CH), 55.7 (Me), 42.2 (CH2), 25.4 (CH2), 2 x C not observed

The synthetic route of 393553-57-6 has been constantly updated, and we look forward to future research findings.

Reference：
Article; Nabi, Ardalan A.; Liyu, Jessica; Lindsay, Ashley C.; Sperry, Jonathan; Tetrahedron; vol. 74; 12; (2018); p. 1199 – 1202;,
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.,90924-06-4

Example 11 O-(7-azabenzotriazol-1-yl)-N,N,N’,N’-tetramethyluronium hexafluorophosphate (113 mg), diisopropylethylamine (0.127 mL), and 4-dimethylaminopyridine in a catalytic amount were added to a mixture of N-cyclopropyl-5,6,7,8-tetrahydrocinnolin-6-amine monohydrochloride (56 mg), 1-methyl-1H-indole-4-carboxylic acid (52 mg), and DMF (2 mL) under an argon gas atmosphere, followed by stirring under heating for 60 hours at an oil temperature of 60 C., and then the resultant was cooled to room temperature. The reaction liquid was diluted with ethyl acetate and then washed with water (3 times) and saturated brine in this order, followed by drying, and concentrating under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol), thereby obtaining N-cyclopropyl-1-methyl-N-(5,6,7,8-tetrahydrocinnolin-6-yl)-1H-indole-4-carboxamide (9.3 mg).

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

Reference：
Patent; ASTELLAS PHARMA INC.; Kawakami, Shimpei; Sakurai, Minoru; Kawano, Noriyuki; Suzuki, Takayuki; Shiraishi, Nobuyuki; Hamaguchi, Wataru; Sekioka, Ryuichi; Moritomo, Hiroyuki; Motitomo, Ayako; US2014/249151; (2014); 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.10075-48-6,5-Bromo-3-methyl-1H-indole,as a common compound, the synthetic route is as follows.

Step B: 5-Bromo-1,3-dimethylindole To a stirred solution of 5-bromo-3-methylindole (2.85 g., 13.6 mmol., 1eq.) in DMF (35 mL.) was added NaH (651 mg. of a 60% dispersion in oil, 16.28 mmol., 1.2 eq.). The mixture was stirred 15 minutes. To this mixture was added iodomethane (0.930 mL., 14.93 mmol., 1.1 eq.). The mixture was stirred for 2 hours. The DMF was removed in vacuo. The residue was diluted with water and extracted 4* with Et2 O. The organic extracts were combined, dried over anhydrous MgSO4, filtered and concentrated in vacuo giving 3.04 g. 5-bromo-1,3-dimethylindole as a reddish liquid.

10075-48-6, As the paragraph descriping shows that 10075-48-6 is playing an increasingly important role.

Reference：
Patent; Merck & Co., Inc.; US5349061; (1994); 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.1204-32-6,Methyl 1-Methylindole-6-carboxylate,as a common compound, the synthetic route is as follows.

Step 2: 1-Methyl-lH-indole-6-carboxylic acid (167) [0334] Methyl 1-METHYL-LH-INDOLE-6-CARBOXYLATE 166 (1.24 MMOL) was stirred with sodium hydroxide (0.59g, 14.88 MMOL) in a 2: 2: 1 mixture of methanol/THF/water (7.5 mL) for 36 hrs at rt to form a precipitate which was collected by filtration and LYOPHILIZED overnight to give the title compound 167 (0.54g, 99percent yield). MS: 175.06 (CALC), 176.1 (OBS).

1204-32-6, The synthetic route of 1204-32-6 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; METHYLGENE, INC.; WO2005/30704; (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

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

General procedure: The relevant indole-3-carboxaldehyde (2a-c, 10 mmol) in THF(25 mL) was added dropwise to a stirred solution of NaH (25 mmol)in THF (25 mL) at 0 C and CH3I (13.2 mmol) was added after 15 minstirring. The reaction mixturewas moved to room temperature andstirred for further 24 h. Then the solvent was removed in vacuumand the residue was extracted by ethyl acetate. The organic layerwas washed with brine, dried over anhydrous sodium sulfate,filtered and concentrated in vacuum. Recrystallization affordedcompound 3a-c with yields of 93.4-97.5%., 10601-19-1

As the paragraph descriping shows that 10601-19-1 is playing an increasingly important role.

Reference：
Article; Chen, Kun; Zhang, Ya-Liang; Fan, Jing; Ma, Xiang; Qin, Ya-Juan; Zhu, Hai-Liang; European Journal of Medicinal Chemistry; vol. 156; (2018); p. 722 – 737;,
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

2532-74-3, 2-(1-Methyl-1H-indol-3-yl)ethanol is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of 3.64 g 1-methyl-3-(2-hydroxyethyl)indole, 18 g methyltriphenoxyphosphonium iodide (J.O.C. 35 2323) and 75 ml dry N,N-dimethylformamide is stirred 2.5 hours at room temperature. Then 5 ml methanol are added, and the mixture is stirred 30 minutes. The mixture is poured into 500 ml dichloromethane and is washed successively with 50 ml portions of 5% aquous sodium thiosulfate, 10% NaOH, and water. The organic layer is dried briefly over magnesium sulfate and most of the solvent removed by evaporation, affording 1-methyl-3-(2-iodoethyl)indole., 2532-74-3

The synthetic route of 2532-74-3 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Syntex (U.S.A.) Inc.; US4255432; (1981); 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

343-90-8, 1-(5-Fluoro-1H-indol-3-yl)-N,N-dimethylmethanamine is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: To a stirred mixture of S1 (R = H, F, Br, or OMe; 5.20 mmol) and diethyl malonate (4.85 mmol) in Et2O (2.6mL) was added dropwise ethyl propiolate (5.20 mmol) at room temperature. The mixture was stirred for 45 min atthis temperature, followed by quenching with H2O. The whole was extracted with Et2O. The extract was washedsuccessively with H2O and brine, and dried over MgSO4. The filtrate was concentrated under reduced pressure togive an oily residue, which was purified by flash chromatography over silica gel with n-hexane-EtOAc (8:1) togive the corresponding S2 as a pale yellow needle., 343-90-8

The synthetic route of 343-90-8 has been constantly updated, and we look forward to future research findings.

Reference：
Article; Iwata, Akira; Inuki, Shinsuke; Oishi, Shinya; Fujii, Nobutaka; Ohno, Hiroaki; Tetrahedron; vol. 71; 37; (2015); p. 6580 – 6585;,
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.399-67-7,7-Fluoro-1H-indole-2-carboxylic acid,as a common compound, the synthetic route is as follows.

General procedure: To a solution of the appropriate 1H-indole-2-carboxylic acid 1 (5 mmol) in Et2O (20 mL) at 0C was added MeLi (10.9 mL, 1.6M in Et2O, 17.4 mmol) dropwise. The mixture reaction was refluxed for 2 h, cooled to room temperature and neutralized with 10% aqueous hydrochloric acid. The organic layer was separated and the aqueous layer was extracted with EtOAc (3?15 mL). The organic phases were combined, washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude product was purified by flash column chromatography using 80/20 hexanes/EtOAc to yield the 1-(1H-indol-2-yl)ethanone 3., 399-67-7

As the paragraph descriping shows that 399-67-7 is playing an increasingly important role.

Reference：
Article; Kumar, Nag S.; Amandoron, Emily A.; Cherkasov, Artem; Brett Finlay; Gong, Huansheng; Jackson, Linda; Kaur, Sukhbir; Lian, Tian; Moreau, Anne; Labriere, Christophe; Reiner, Neil E.; See, Raymond H.; Strynadka, Natalie C.; Thorson, Lisa; Wong, Edwin W.Y.; Worrall, Liam; Zoraghi, Roya; Young, Robert N.; Bioorganic and Medicinal Chemistry; vol. 20; 24; (2012); p. 7069 – 7082;,
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