Indole Building Blocks

933-67-5, 7-Methyl-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: Trifluoromethyl ketone (0.3mmol),trifluoromethanesulfonicacid (9mg, 0.06mmol) were added to a dry sealed tube charged with indole(0.9mmol) and sodium sulphate anhydrous (12.8mg, 0.09mmol) under argon. Thereaction mixture was stirred at 115C for 12h. After the reaction was completed, the mixture was purifiedby column chromatography on silica gel with hexanes/ethyl acetate as eluent.The desired product was obtained as white or pale yellow solid. Isolated yield: 82%. White solid. M.P.: 116-120oC.1H NMR (400 MHz, CDCl3) delta 8.10 (s, 2 H), 7.44 (d, J= 2.0 Hz, 2 H), 6.82 (d, J = 6.8 Hz, 2 H), 6.68-6.60 (m, 4 H), 2.46(s, 6 H), 2.02-1.95 (m, 1 H), 0.59-0.54 (m, 2 H), 0.29-0.25 (m, 2 H); 19FNMR (375 MHz, CDCl3) delta -69.53 (s, 3 F); 13C NMR(100.7 MHz, CDCl3) delta 135.6, 128.6 (q, J = 284.8 Hz), 126.7,124.3 (q, J = 2.2 Hz), 122.1, 119.8, 119.4, 119.3, 50.4 (q, J = 26.0Hz), 16.5, 15.4 (q, J = 2.2 Hz), 2.2 ppm. IR (KBr): nu = 3415, 3050,3012, 2959, 2922, 2855, 1615, 1541, 1495, 1457, 1431, 1409, 1380, 1345, 1319,1251, 1185, 1147, 1123, 1098, 1068, 1028, 1017, 994, 960, 924, 883, 844, 817,782, 750, 723, 581, 516, 483, 458 cm-1. MS (EI): m/z (%) 382(M , 100), 354, 313, 251,157, 144, 57. HRMS: Calculated for C23H21F3N2: 382.1657; Found: 382.1652

The synthetic route of 933-67-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Wang, Yi; Yuan; Xing, Chun-Hui; Lu, Long; Tetrahedron Letters; vol. 55; 5; (2014); p. 1045 – 1048;,
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.51417-51-7,7-Bromoindole,as a common compound, the synthetic route is as follows.

196 mg (1 mmol) of 7-bromoindole, 122.4 mg (1.2 mmol) of 5-hydroxy-2-pentanone and 25.6 mg (0.05 mmol) of tris(pentafluorophenyl)boron were added to a 10 mL reaction tube.Stir the reaction at 40 C and monitor by TLC until the sputum disappears.The reaction mixture was extracted with 3¡Á20 mL ethyl acetate.Combine the organic phase,Wash with saturated brine and dry over anhydrous sodium sulfate.Evaporation of the solvent ethyl acetate under reduced pressure and chromatography (ethyl ether: ethyl acetate = 20:1) to give 3-(tetrahydro-2-methyl-2-furanyl)-7-bromo 1H-indole The hydrazine product was 258 mg, yield: 92%.

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

Reference£º
Patent; Huazhong University of Science and Technology; Wang Shijun; Xia Sang; Tang Xiangying; (18 pag.)CN109912579; (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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.348-36-7,Ethyl 5-fluoro-1H-indole-2-carboxylate,as a common compound, the synthetic route is as follows.

60percent Sodium hydride (197mg, 4.96mmol) was dissolved in 17mL of N, N-dimethylformamide, cooled down to 0¡ãC, ethyl 5-fluoro-1H-indole-2-carboxylate 11b (857mg, 4.14mmol) was added, stirred until there’s no bubbles generated, phenylsulfonyl chloride (0.59mL, 4.59mmol) was added dropwise to be dissolved in 3 mL of N, N-dimethylformamide solution, and the reaction was carried out in an ice bath for 1 hour after the completion of addition. 50mL of water and 100mL of ethyl acetate were added to the reaction solution, the pH was adjusted to neutral with saturated sodium bicarbonate solution. The organic phase was washed with water (50mL*3), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (developing agent: system C) to obtain ethyl 5-fluoro-1-(phenylsulfonyl)-1H-indole-2-carboxylate 11c (1.40g, pale yellow solid), yield: 97.5percent. MS m / z (ESI): 347.9 [M + 1]

As the paragraph descriping shows that 348-36-7 is playing an increasingly important role.

Reference£º
Patent; Zhejiang Hisun Pharmaceutical Co., Ltd; CHEN, Lei; GUAN, Dongliang; BAI, Hua; YAN, Xing; MIAO, Shuai; ZHU, Songsong; (54 pag.)EP3339305; (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

16096-32-5, 4-Methyl-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

(1) 4-methylindole 0.5 mmol, sodium trifluoromethanesulfinate 1.0 mmol,Triphosaldehyde 1.0 mmol was added to 3 mL of acetonitrile, and the reaction was stirred for 2 hours under ice bath.(2) After the reaction was completed, the reaction was quenched by adding 10 mL of a 5% aqueous NaOH solution.Extract twice with ethyl acetate (15 mL ¡Á 2), wash once with saturated brine.Ethyl acetate was distilled off under reduced pressure. Column chromatography gave the product as a pale yellow solid.The yield was 76%.

16096-32-5 4-Methyl-1H-indole 85282, aindole-building-block compound, is more and more widely used in various.

Reference£º
Patent; Lishui College; Yuan Yanqin; Guo Shengrong; Yang Minghua; (28 pag.)CN108586312; (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

29906-67-0, 1-Methyl-5-nitro-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

10% Pd/C (0.18 g/g of startingmaterial) was added to a solution of starting material dissolved inTHF (54 mL/g of starting material). Reaction flask was sealed andvacuum was used to remove air. A balloon filled with hydrogen gaswas then attached to the flask. The reaction was stirred at roomtemperature for 24e48 h or until disappearance of starting materialwas observed by TLC. The reaction was then filtered through celite.Filtrate was rotovapped to give a brown solid; 100%; 1H NMR(DMSO): delta 7.15-7.05 (m, 2H), 6.71 (dd, J 3.0, 0.9 Hz, 1H), 6.57 (dd,J 8.5, 2.1 Hz, 1H), 6.12 (dd, J 3.0, 0.9 Hz, 1H), 3.67 (s, 3H); 13CNMR (DMSO): delta141.30, 131.12, 129.49, 129.44, 129.41, 112.31, 110.11,104.21, 99.13, 32.86.

The synthetic route of 29906-67-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Martinez, Anastasia A.; Espinosa, Bianca A.; Adamek, Rebecca N.; Thomas, Brent A.; Chau, Jennifer; Gonzalez, Edwardo; Keppetipola, Niroshika; Salzameda, Nicholas T.; European Journal of Medicinal Chemistry; vol. 157; (2018); p. 1202 – 1213;,
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

1215-59-4, 5-(Benzyloxy)-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a stirred solution of phosphorus oxychloride (2.29 mL, 24.6 mmol) in DMF (15 mL), was added a solution of 5-benzyloxyindole (5.00 g, 22.4 mmol) in DMF (20 mL) at room temperature. After 30 min, the reaction mixture was poured into ice-water (50 mL). To this mixture was added solid NaOH (4.80 g, 0.112 mol) and water (50 mL). The precipitate was collected, washed with EtOH, and dried to give 4.67 g (83%) of compound 6o. 1H NMR (400 MHz, DMSO-d6) delta 12.01 (s, 1H), 9.89 (s, 1H), 8.21 (s, 1H), 7.68 (m, 1H), 7.49-7.30 (m, 6H), 6.97 (m, 1H), 5.12 (s, 2H) ppm; MS (m/e) 251 (M), 252 (M+H).

The synthetic route of 1215-59-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Cephalon, Inc.; US2007/299061; (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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.10075-50-0,5-Bromoindole,as a common compound, the synthetic route is as follows.

General procedure: NaH (6.1 mmol, 1.2 equiv) was slowly added to a solution of 5-bromoindole/indazole (5.1 mmol,1 equiv) in DMF (10 mL) at 0 ¡ãC. The mixture was stirred at 0 ¡ãC for 10 min then the alkylhalide (6.1 mmol, 1.2 equiv) was added at the same temperature. The reaction mixture wascontinued to stir at rt for 2 h. When the reaction was complete [TLC (EtOAc/hexane 1:5)], themixture was extracted with EtOAc (2 ¡Á 20 mL) and washed with water (2 ¡Á 20 mL). The organiclayer was separated, dried over anhydrous Na2SO4 and the solvent removed under reducedpressure. The residue obtained was purified by flash column chromatography [silica gel (230?400 mesh; Merck), EtOAc/hexane 1:5].

The synthetic route of 10075-50-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Narayanarao, Manjunatha; Koodlur, Lokesh; Revanasiddappa, Vijayakumar G.; Gopal, Subramanya; Kamila, Susmita; Beilstein Journal of Organic Chemistry; vol. 12; (2016); p. 2893 – 2897;,
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.16732-70-0,Ethyl 5-bromo-1H-indole-2-carboxylate,as a common compound, the synthetic route is as follows.

A mixture of 5-bromoindole-2-carboxylic acid ethyl ester (3.48 g, 13 mmol), 4-tert-butylphenylboronic acid (4.63 g, 26 mmol), K3P04 (9.93 g, 45 mmol), Pd(OAc)2 (146 mg, 0.65 mmol), tri-o-tolylphosphine (396 mg, 1.3 mmol), EtOH (20 ml) and toluene (10 mL) was stirred under argon for 20 min at room temperature, and then heated at 100C for 24 h. The mixture was allowed to cool, poured into NaHC03 (aq. , sat. ) and extracted with EtOAc. The combined extracts were washed with water and brine and then dried over Na2S04. Concentration and purification by chromatography gave the sub-title compound (3.27 g, 78%).

16732-70-0 Ethyl 5-bromo-1H-indole-2-carboxylate 259091, aindole-building-block compound, is more and more widely used in various.

Reference£º
Patent; BIOLIPOX AB; WO2005/123675; (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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.35320-67-3,2-Methyl-1H-indol-4-ol,as a common compound, the synthetic route is as follows.

4-Hydroxy-2-methylindole (1.00 g, 6.79 mmol) was taken up in dry CH2Cl2 (10 mL). Triethylamine (1.40 mL, 12.2 mmol) was added and the solution was cooled to 0 C. in an ice bath. A solution of trifluoromethanesulfonic acid anhydride (1.23 mL, 7.47 mmol) in CH2Cl2 (2 mL) was added drop-wise. The reaction mixture was stirred for 10 min at 0 C. and was diluted with CHCl3 and extracted with sat. K2CO3. The organic layer was dried over K2CO3, filtered and concentrated under reduced pressure. The residue was taken up in dry THF (3 mL) and sodium hydride (60% dispersion, 360 mg, 9.00 mmol) was added portion wise. After the hydrogen evolution had ceased, a solution of tert-butyldimethylsilyl chloride (1.13 g, 7.50 mmol) in dry THF (2 mL) was added and the mixture was stirred overnight at room temperature. The reaction mixture was diluted with CH2Cl2 (20 mL), washed with sat. NH4Cl solution (10 mL), dried (Na2SO4), filtered and concentrated to provide the crude product. Flash chromatography (SiO2, AcOEt/heptane 1:50) gave pure trifluoro-methanesulfonic acid 1-(tert-butyl-dimethyl-silanyl)-2-methyl-1H-indol-4-yl ester (1.70 g, 64%).

The synthetic route of 35320-67-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Kelly, Martha; Lee, Younghee; Liu, Bin; Fujimoto, Ted; Freundlich, Joel; Dorsey, Bruce D.; Flynn, Gary A.; Husain, Arifa; US2006/270686; (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

288385-88-6, 4-Fluoro-5-hydroxy-2-methylindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

4-amino-6-chloro-pyrimidine-5-carbaldehyde Compound Ia (1.4 g), 4-fluoro-2- methyl-lH-indol-5-ol Compound Ib (1.3 g), Cs2CO3 (5.8 g) and DMSO (10 mL) were added to a flask.The mixture was stirred at rt for 2 hrs, then poured into water and extracted with EtOAc. The organic layer was separated, dried with MgSO4, then concentrated and the residue was purified by flash chromatography (CH2Cl2:MeOH/9.5:0.5) to afford 4- amino-6-(4-fluoro-2-methyl- 1 H-indol-5 -yloxy)-pyrimidine-5 -carbaldehyde Compound Ic (2.2 g, 94%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) delta 11.30 (s, IH),10.40 (s, IH), 8.55 (s, IH), 8.40 (s, IH), 8.10 (s, IH), 7.05 (d, IH), 6.85 (t, IH), 6.20 (s, IH), 2.40 (s, 3H). MS (ESI) m/z: 285 (M+H+).

As the paragraph descriping shows that 288385-88-6 is playing an increasingly important role.

Reference£º
Patent; JANSSEN PHARMACEUTICA, N.V.; WO2007/109783; (2007); A2;,
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