Tag: M.W:100-200

5192-23-4, 4-Aminoindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

EXAMPLE 19. N-(3-(9H-PURGammaN-6-YL)PYRIDGammaN-2-YL)- 1H-LNDOL-4-AMGammaNE [00165] 6-(2-Fluoropyridin-3-yl)-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (115.0 mg, 0.3842 mmol) and lH-indol-4-amine (Aldrich, St. Louis, MO, 70.7 mg, 0.535 mmol) were suspended in EtOH (1.8 mL) and aqueous hydrochoric acid (5.0 M, 0.090 ml, 0.45 mmol) was added. The flask was fitted with a reflux condenser and placed in a preheated oil bath (100 0C), and the reaction was stirred for 3 hours. Then, the reaction was cooled to room temperature and diluted with DCM, 2 N ammonia in MeOH, EtOH, and MeOH and concentrated. The residue was treated with MeOH and filtered. Neither the filtrate nor the solid contained pure material, so they were combined, concentrated, treated with DMF, and filtered. The filtrate was concentrated and purified on HPLC (10% to 100% MeCN / water with 0.1% TFA over 30 minutes with a total flow rate of 100 mL/min). The fractions with product were collected, concentrated, and filtered through a silica gel plug (about 1 inch, 50: 1 DCM / 2 N ammonia in MeOH to 20: 1 DCM / 2 N ammonia in MeOH to 5: 1 DCM / 2 N ammonia in MeOH) to afford N-(3-(9H-purin-6-yl)pyridin-2-yl)-lH-indol-4-amine (6.9 mg, 5% yield). MS (ESI pos. ion) m/z: 328, (M+H)+. 1H NMR (d6-DMSO, 400 MHz) delta 12.90 (s, IH), 11.16 (s, IH), 9.87 (d, J = 7.82 Hz, IH), 9.24 (s, IH), 8.73 (s, IH), 8.43 (dd, J = 4.69 Hz, 1.96 Hz, IH), 8.28 (dd, J = 4.6 Hz, 3.81 Hz, IH), 7.38 – 7.35 (m, IH), 7.09 (s, IH), 7.08 – 7.06 (m, IH), 7.04 (dd, J = 7.82 Hz, 4.69 Hz, IH), 6.79 – 6.76 (m, IH)., 5192-23-4

The synthetic route of 5192-23-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; AMGEN INC.; ANDREWS, Kristin; BO, Yunxin, Y.; BOOKER, Shon; CEE, Victor, J.; D’ANGELO, Noel; HERBERICH, Bradley, J.; HONG, Fang-Tsao; JACKSON, Claire, L., M.; LANMAN, Brian, A.; LIAO, Hongyu; LIU, Longbin; NISHIMURA, Nobuko; NORMAN, Mark, H.; PETTUS, Liping, H.; REED, Anthony, B.; SMITH, Adrian, L.; TADESSE, Seifu; TAMAYO, Nuria, A.; WU, Bin; WURZ, Ryan; YANG, Kevin; WO2010/126895; (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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1953-54-4,5-Hydroxyindole,as a common compound, the synthetic route is as follows.

EXAMPLE 10 Preparation of 4-(1H-indol-5-yloxy)-2-phenylthieno[2,3-b]pyridine-5-carbonitrile 130 A mixture of 4-chloro-2-phenylthieno[2,3-b]pyridine-5-carbonitrile 20 (120 mg, 0.44 mmol), 5-hydroxyindole (71 mg, 0.53 mmol) and potassium carbonate (91 mg, 0.66 mmol) in 4 mL of acetonitrile was heated at 80 C. for 5 hours. The reaction mixture was cooled and diluted with 10 mL of water. The precipitate was collected by filtration and washed with water followed by diethyl ether to give 127 mg (79%) of 4-(1H-indol-5-yloxy)-2-phenylthieno[2,3-b]pyridine-5-carbonitrile 130 as an off-white solid, mp 219-221 C., MS 368.1 (M+H)+., 1953-54-4

As the paragraph descriping shows that 1953-54-4 is playing an increasingly important role.

Reference£º
Patent; Boschelli, Diane H.; Cole, Derek C.; Asselin, Magda; Barrios Sosa, Ana C.; Wu, Biqi; Tumey, Lawrence N.; US2007/82880; (2007); 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

51417-51-7,51417-51-7, 7-Bromoindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 1: Synthesis of 2(E)-methyl3-(1H-indol-7-yl)acrylate 7-Bromoindole (5.0 g, 25.5 mmol), methyl acrylate (4.6 ml, 51.1 mmol), triphenylphosphine (0.55 g, 2.10 mmol), N,N-diisopropylethylamine (5.8 ml, 42.3 mmol), and palladium (II) acetate (0.25 g, 1.11 mmol) were added to N,N-dimethylformamide (50 ml), and the mixture was stirred at 70 C. for 18 hours under a stream of nitrogen. After cooling to room temperature, methyl acrylate (4.6 ml, 51.1 mmol), triphenylphosphine (0.55 g, 2.10 mmol), and palladium (II) acetate (0.25 g, 1.11 mmol) were added to the reaction mixture, and the mixture was stirred at 75 C. for 47 hours under a stream of nitrogen. After cooling to room temperature, methyl acrylate (7.0 ml, 77.7 mmol), triphenylphosphine (0.88 g, 3.36 mmol), and palladium (II) acetate (0.40 g, 1.78 mmol) were added to the reaction mixture, and the mixture was stirred at 100 C. for 95 hours under a stream of nitrogen. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. To the obtained residue, a hexane/ethyl acetate mixed solution (1:1, 300 ml) was added, and the organic layer was washed with water. The obtained aqueous layer was subjected to extraction with a hexane/ethyl acetate (1:1) mixed solution, and the combined organic layer was washed with saturated saline. The obtained organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography (eluent; hexane:ethyl acetate=6:1) to obtain 2 (E)-methyl 3-(1H-indol-7-yl)acrylate (3.46 g, 67%) as a pale yellow-brown solid. ESI-MS: m/z 202 [M+H]+. 1H-NMR (CDCl3) delta: 3.85 (3H, s), 6.52 (1H, d, J=16.0 Hz), 6.62 (1H, dd, J=2.9, 2.0 Hz), 7.16 (1H, t, J=7.6 Hz), 7.28 (1H, t, J=2.9 Hz), 7.43 (1H, d, J=7.6 Hz), 7.71 (1H, d, J=7.6 Hz), 8.04 (1H, d, J=16.0 Hz), 8.59 (1H, br s).

51417-51-7 7-Bromoindole 2757020, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Patent; ArQule, Inc.; US2012/165278; (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.6146-52-7,5-Nitroindole,as a common compound, the synthetic route is as follows.,6146-52-7

To a solution of 5 -nitro-1 H-indole (2.Og, 12.3mmol) in acetone (20ml), powdered potassium hydroxide (3.4g, 60.7mmol, 5eq) was added followed by the addition methyl iodide (2.6 Ig, 18.5mmol, 1.5eq) at O0C. The reaction mixture was heated to reflux for 10 hr. The solvent was evaporated and water was added. The compound was extracted with ethyl acetate, dried over anhydrous sodium sulphate, filtered and the organic layer was concentrated to dryness to yield l-methyl-5 -nitro-1 H-indole (2.Og, 92%). The crude compound was used in the next stage without purification.

6146-52-7 5-Nitroindole 22523, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Patent; F2G LTD; WO2006/123145; (2006); 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.16136-52-0,4-Cyanoindole,as a common compound, the synthetic route is as follows.

EXAMPLE 88 1-Benzyl-4-cyanoindole Following a procedure and using relative proportions of starting materials similar to those described in Example 65, but using 4-cyanoindole as starting material, the title compound was obtained in a yield of 94%. Nuclear Magnetic Resonance Spectrum (CDCl3, 270 MHz), delta ppm: 5.37 (2H, singlet), 6.77 (1H, doublet, J=3.4 Hz), 7.05-7.50 (9H, multiplet).

16136-52-0, 16136-52-0 4-Cyanoindole 3817602, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Patent; Sankyo Company, Limited; US5877199; (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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.766557-02-2,6-Chloro-1H-indole-3-carboxylic acid,as a common compound, the synthetic route is as follows.,766557-02-2

To a stirred solution of indolic amine (Id) (93 mg, 0.3 mmol) and 6-chloro-lH-indole-3- carboxylic acid (2e) (65 mg, 0.33 mmol) in 5 mL of dry CH2C12, l-ethyl-3-(3- dimethylaminopropyl) carbodiimide (EDCI, 5 mg, 0.33 mmol) was added at room temperature. The resulting mixture was stirred overnight. CH2C12 was evaporated then EtOAc (20 mL) and a 1M aqueous solution of hydrochloric acid (20 mL) were added. After extraction, the organic phase was washed with a 1M aqueous hydrochloric acid, a 5% aqueous solution of Na2C03, brine, dried over anhydrous MgS04, filtered and concentrated under vacuum. Purification of the resulting crude product by column chromatography using EtOAc-pentane (from 10/90 to 80/20) yielded pure bis-indole 6b (90 mg, 0.185 mmol) as a beige foam. Yield: 62%.IR (neat): 3410, 3270, 2970, 2930, 1685, 1620, 1530, 1445, 1365, 1160, 850, 795 cm”1. 1H NMR (300 MHz, CDC13): delta = 1.36 (s, 9H), 3.57-3.63 (m, 2H), 5.22-5.28 (m, 1H), 5.40-5.45 (m, 1H),6.89- 7.19 (m, 6H), 7.42-7.54 (m, 2H), 7.96-8.01 (s, 1H), 9.01 (s, 1H), 9.61 (s, 1H) ppm. 13C NMR (75.5 MHz, CDC13): delta = 27.7 (3C), 44.1, 47.3, 79.4 (C), 110.5, 1 11.3, 112.2, 113.4, 117.9, 121.2, 121.3, 121.7, 123.3, 123.8, 124.6, 126.7, 128.0, 128.3, 134.8, 136.7, 157.5, 165.8 ppm. LRMS (ESI): m/z (%) = 509 (32) [(M+Na)+], 237 (100).

The synthetic route of 766557-02-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; UNIVERSITE JOSEPH FOURIER; DENIS, Jean-Noel; JOLIVALT, Claude, Marcelle; MAURIN, Max, Maurin, Louis; JEANTY, Matthieu; WO2013/14102; (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.1805-65-8,2-(tert-Butyl)-1H-indole,as a common compound, the synthetic route is as follows.

General procedure: In order to verify the feasibility of the reaction, azobenzene derivative 1a and 2-t-butyl-indole 2a as reactants and 10 mol% of phosphoric acid CP1 as a catalyst were reacted in DCM at room temperature as shown in the following formula. The reaction proceeded smoothly to give the shaft chiral arylindole 3a with a yield of 76% and an ee value of 87%. It can be seen that it is feasible to asymmetrically construct the axial chiral arylindole via an indole nucleophilic attack on azobenzene derivatives. Next, the catalysts with different chiral skeletons and substituents are screened. The aromatic ring skeleton and 3,3′-substituent of the catalyst have important influence on enantioselectivity. Among them, catalyst CP4 had the best results in terms of enantioselectivity (92% ee) and yield (99%).Reaction conditions: React with 1 a (0.10 mmol, 1.0 equiv.), 2a (0.12 mmol, 1.2 equiv.) And CP (10 mol%) in dichloromethane (2.0 mL) at room temperature.Further conditions were screened as shown in Table 1 to obtain optimal reaction conditions: 2a (1.1 eq.) Was added to 1a (1.0 eq.), 2.5 mol% CP4, 2.0 mL toluene solution and reacted at room temperature with 97% ee, 95% isolated yield gave the shaft chiral arylindole 3a.

1805-65-8, As the paragraph descriping shows that 1805-65-8 is playing an increasingly important role.

Reference£º
Patent; South University of Science and Technology of China; Tan Bin; Qi Liangwen; Mao Jianhui; (23 pag.)CN107501160; (2017); 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

50820-65-0, Methyl 1H-indole-6-carboxylate is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

50820-65-0, To a DMF (60 mL) solution of methyl 1H-indole-6-carboxylate (5.1 g, 29.1 mmol) at -60 C was added a DMF solution (40 mL) of NBS (5.70 g, 32.0 mmol)dropwise. The reaction mixture was stirred for 2 hours while it was warmed up to room temperature. The reaction mixture was then poured into ice water (1 L) and the precipitate formed was collected through via vacuum filtration. The solid was washed with water. The solid was dissolved in ethyl acetate and washed twice with sat. aq. NaC1. The ethyl acetate layer was separated, dried (Na2504), filtered andconcentrated to give the cmde product. The material was carried on without further purification. LCMS (ESI) m/e 254.1 [(M+H), calcd C10H9Br1N1O2, 253.91; LC/MS retention time (method A): IR = 1.63 mm.

The synthetic route of 50820-65-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; LUO, Guanglin; CHEN, Ling; (83 pag.)WO2017/184658; (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

875-30-9, 1,3-Dimethyl-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

b) 1,3-Dimethyl-1H-indole-2-carboxaldehyde To a stirred solution of phosphorus oxychloride (7.0 mL, 75 mmole) in DMF (25 mL) was added dropwise a solution of 1,3-dimethylindole (12.0 g, 83 mmole) in dry DMF (6.0 mL). The reaction was stirred at RT for 2 hr then was poured onto ice. The mixture was basified with a solution of NaOH (13.2 g, 330 mmole) in H2O (44 mL), then was extracted with Et2O (2x 50 mL). The combined organic layers were washed with brine, dried (MgSO4), and concentrated under vacuum. Flash chromatography on silica gel (10% ethyl acetate/hexanes) gave the title compound (13.03 g, 91 %) as an off-white solid: LCMS (ES) m/e 174.2 (M + H)+; 1H NMR (400 MHz, CDCl3) delta 10.16 (s, 1 H), 7.68 (d, J = 8.1 Hz, 1 H), 7.42 (t, 1 H), 7.32 (d, J = 8.5 Hz, 1 H), 7.15 (t, 1 H), 4.04 (s, 3 H), 2.63 (s, 3 H)., 875-30-9

The synthetic route of 875-30-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Affinium Pharmaceuticals, Inc.; EP1226138; (2004); B1;,
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

35320-67-3, 2-Methyl-1H-indol-4-ol is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a stirred solution of 2-methyl-1H-indol-4-ol (200 mg, 1.36 mmol) in anhydrous dioxane (50 mL) were added N-benzyl-2-chloro-7,8-di -hydro-5H- pyrano[4,3-d]pyrimidin-4-amine (374 mg,1.36 mmol), Pd2dba3 (248 mg, 0.27 mmol), X-Phos (129 mg, 0.27 mmol) and Cs2CO3 (891 mg, 2.72 mmol). The resulting suspension was stirred at 100 oC under N2 for 3 hrs. The reaction was filtered to remove Cs2CO3 and catalyst. The filtrate was concentrated in vacuo to give a brown oil. The crude was purified via silica gel column (hexane/ethyl acetate) to afford 1-[4-(benzylamino)-7,8-dihydro-5H-pyrano[4,3-d]pyrimidin-2- yl]-2-methyl-indol-4-ol (300 mg, 45.7%) as an orange solid. LCMS (M+H+) m/z: Calcd: 387.15; Found: 387.2., 35320-67-3

35320-67-3 2-Methyl-1H-indol-4-ol 590225, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Patent; CLEAVE BIOSCIENCES, INC.; ZHOU, Han-Jie; WUSTROW, David; (498 pag.)WO2016/200840; (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