Month: October 2020

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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1211594-25-0,4-Bromo-1H-indole-7-carboxylic acid,as a common compound, the synthetic route is as follows.

A solution of 4-bromo-1H-indole-7-carboxylic acid (5.5 g, 22.91 mmol) EDC (6.59 g, 34.4 mmol) and HOBt (5.26 g, 34.4 mmol) in THF (150 mL) and DCM (180 mL) was stirred at rt for 1 h. The mixture was then bubbled with NH3 gas for about 15 mm and the resulting mixture was stirred at rt overnight. The mixture was diluted by addition of water and extracted with DCM. The organic phase was washed with brine, dried and concentrated to give a residue, which was suspended in ether and filtered to provide 4-bromo-]H-indole-7-carboxamide (5.3 g, 97%): ?H NMR (DMSO-d6) 3 11.40 (br, 1H), 8.08 (br, 1H), 7.29-7.57 (d, J = 7.6 Hz, 1H), 7.43-7.42 (m, 2H), 7.28-7.26 (d, J = 7.6 Hz, 1H), 6.43-6.42 (m, 1H)., 1211594-25-0

1211594-25-0 4-Bromo-1H-indole-7-carboxylic acid 59267539, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Patent; ABBVIE INC.; BONAFOUX, Dominique; DAVIS, Heather, M.; FRANK, Kristine, E.; FRIEDMAN, Michael, M.; HEROLD, J., Martin; HOEMANN, Michael, Z.; HUNTLEY, Raymond; OSUMA, Augustine; SHEPPARD, George; SOMAL, Gagandeep, K.; VAN CAMP, Jennifer; VAN EPPS, Stacy, A.; VASUDEVAN, Anil; WALLACE, Grier, A.; WANG, Lu; WANG, Zhi; WILSON, Noel, S.; XU, Xiangdong; WO2014/210255; (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

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

111258-23-2, Methyl 4-methoxy-1H-indole-2-carboxylate is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,111258-23-2

Example 27A Methyl 1-cyanomethyl-4-methoxy-1H-indole-2-carboxylate Starting with 5.0 g (24.4 mmol) of methyl 4-methoxyindole-2-carboxylate, the general procedure [K] gives 5.6 g (92% of theory) of product. HPLC (method 1): Rt=4.34 min MS (ESIpos): m/z=245 (M+H)+

111258-23-2 Methyl 4-methoxy-1H-indole-2-carboxylate 688172, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Patent; Bayer HealthCare AG; US2007/185121; (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

81224-16-0, 7-Bromo-4-methoxy-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

81224-16-0, To a flame-dried flask containing 10a5 (50.0 mg, 0.233 mmol) in anhyd. THF (600 muL), added oxalyl chloride (97 muL, 1.11 mmol, 5 equiv) and let stir under an atmosphere of N2 until TLC (5:1 hexanes/EtOAc) indicated consumption of starting material (5-12 hr, depending on scale). All volatiles were removed by rotoevaporation and resulting green residue was immediately suspended in anhyd. THF (1 mL), followed by the addition of N-Boc piperazine6 (52 mg, 0.28 mmol, 1.2 equiv) and DIPEA (78 muL, 2 equiv). Resulting mixture was stirred under an atmosphere of N2 at RT for 12 hr. and then at reflux for 30 min (if needed) when TLC (5:1 hexanes/EtOAc) indicated reaction completion. Reaction was allowed to cool to RT, poured into H2O (10 mL) and extracted with EtOAc (3¡Á10 mL). The combined organic layers were dried over anhyd. MgSO4, filtered, and all solvents were evaporated. Crude 18 was purified by flash chromatography (CombiFlash Automated Chromatographer, 12 g column, dryloaded with 4 g pre-packed dry loading column. Run using 100% Hexanes to 50% EtOAc:Hexanes gradient over 30 column volumes, followed by EtOAc flush) to yield 18 as a light brown powder (78 mg, 75%). 1H NMR (400 MHz, CDCl3) delta 9.44 (s, 1H), 7.94 (d, J=3.1, 1H), 7.28 (d, J=8.5, 1H), 6.56 (d, J=8.5, 1H), 3.90 (s, 3H), 3.71 (m, 2H), 3.60-3.51 (m, 2H), 3.46 (m, 4H), 1.47 (s, 9H). (ES+) m/z (M+H)+ 466; (M+Na)+ 488; Rt=1.34. 5. US PATENT: US200300692456. Faust, A.; Waschkau, B.; Waldeck, J.; Holtke, C.; Breyholtz, H.; Wagner, S.; Kopka, K.; Heindel, W.; Schafer, M.; Bremer, C. Bioconjug. Chem. 2008, 19, 1001-1008.

As the paragraph descriping shows that 81224-16-0 is playing an increasingly important role.

Reference£º
Patent; Yale University; US2012/269766; (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

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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.98600-34-1,4-Bromoindole-3-carboxyaldehyde,as a common compound, the synthetic route is as follows.

Example 43 N4-(5-Cyclopropyl- 1 H-pyrazol-3 -yl)-N2-((3 -methyl- 1 H-indol-4-yl)methyl)pyrimidine-2,4-diamine (1-92) step 1 : To a refluxing solution of 4-bromo-lH-indole-3-carbaldehyde (644 mg, 2.87 mmol) in dry THF (20 mL) was added LiAlH4 (218 mg, 5.75 mmol) in several small portions. Heating at reflux was continued for 1 h, the reaction cooled to RT and quenched with water (220 mu?^), 15 % aq. NaOH (w/w, 220 mu? ), and water (650 mu?^). The resulting precipitate was filtered and the filtrate was concentrated under reduced pressure to dryness. To the residue was added aq. NaOH (10 mL) and the solution twice extracted with DCM (2 x 10 mL). The combined extracts were dried (MgSO i), filtered and concentrated in vacuo to afford 454 mg (75%) of 4-bromo-3 -methyl- lH-indole (230) as light brown oil: MS (ESI) m/z = 210.1 [M+l] +, 98600-34-1

As the paragraph descriping shows that 98600-34-1 is playing an increasingly important role.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; ALIAGAS-MARTIN, Ignacio; CRAWFORD, James; LEE, Wendy; MATHIEU, Simon; RUDOLPH, Joachim; WO2013/26914; (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.98600-34-1,4-Bromoindole-3-carboxyaldehyde,as a common compound, the synthetic route is as follows.

-Acetyl-4-bromo-l,2-dihydro-indol-3-one: 4-Bromo-lH-indole-3-carbaldehyde (4.0 g, 17.8 mmol) was stirred in acetic anhydride (20 mL) at reflux for 4h. The reaction was cooled and concentrated in vacuo. Cold MeOH was added to precipitate a white solid, whi, 98600-34-1

98600-34-1 4-Bromoindole-3-carboxyaldehyde 2763178, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2009/129401; (2009); 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

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