Day: March 17, 2022

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.213682-04-3,4-Methoxy-1H-indole-2-carbaldehyde,as a common compound, the synthetic route is as follows.

Example 84 COMPOUND IN-076 3-(4-Methoxy-1H-indol-2-ylmethylene)-2-oxo-2,3-dihydro-1H-indole-5-sulfonic acid methylamide A mixture of 2-oxo-2,3-dihydro-1H-indole-5-sulfonic acid methylamide (194 mg, 0.86 mmol), 4-methoxy-1H-indole-2-carbaldehyde (150 mg, 0.86 mmol) and piperidine (36 mg, 0.43 mmol) in ethanol (0.2M) was stirred at room temperature for a total of 5 days. The reaction was concentrated to 1/4 of its volume and the precipitate was collected by vacuum filtration to give the title compound as a pale orangish-red solid. 1H-NMR (360 MHz, DMSO-d6) delta 12.82 (s, 1H, NH), 11.36 (br s, 1h, NH), 8.11(s, 1H-H-vinyl), 8.11 (d, J=1.3 Hz, 1H), 7.63 (dd, J=1.3 & 8.5 Hz, 1H), 7.15-7.27 (m, 4H), 7.08 (d, J=7.96 Hz, 1H), 6.56 (d, J=7.7 Hz, 1H), 3.92 (s, 3H, OCH3), 2.43 (d, J=5.02 Hz, 3H, NCH3). MS m/z 384 [M++1].

213682-04-3, 213682-04-3 4-Methoxy-1H-indole-2-carbaldehyde 10678838, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; Tang, Peng Cho; Harris, G. Davis; Li, Xiaoyuan; US2002/52369; (2002); 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

A solution of 5-methoxyindole-3-carboxaldehyde (80 g) in dimethylformamide (1 L) under nitrogen was treated portion-wise with sodium hydride (20.1 g, 60% dispersion in mineral oil) over 15 minutes. After stirring at ambient temperature for 30 minutes the mixture was treated dropwise with methyl iodide (31.3 mL) over 10 minutes and stirring was then continued for a further 2 hours. The reaction mixture was poured cautiously into water then extracted with ethyl acetate. The organic phase was washed with water, then dried over sodium sulfate and then evaporated. The residue was triturated with pentane to give the title compound (76 g) as a pale brown solid, m.p. 133-134 C. 1H NMR [(CD3)2SO]: delta 9.86 (1H, s); 8.20 (1H, s); 7.60 (1H, d, J=2.6 Hz); 7.50 (1H, d, J=8.9 Hz); 6.96 (1H, dd, J=8.9 and 2.6 Hz); 3.86 and 3.80 (6H, s)., 10601-19-1

10601-19-1 5-Methoxy-1H-indole-3-carbaldehyde 82758, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; Cox, Paul J.; Majid, Tahir N.; Lai, Justine Y.Q.; Morley, Andrew D.; Amendola, Shelley; Deprets, Stephanie D.; Edlin, Christopher; US2004/9983; (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

434958-85-7,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.434958-85-7,N-Boc-5-Hydroxyindole,as a common compound, the synthetic route is as follows.

To a solution of Intermediate 49 (3.00 g, 12.9 mmol, 1.0 eq) in anhydrous MeCN (13 mL) was added a solution of N-bromosuccinimide (2.53 g, 14.2 mmol, 1.1 eq) in anhydrous MeCN (130 mL) dropwise via cannula. After 1.5 h, addition was complete and the reaction mixture was stirred for a further 1 h. The reactionmixture was concentrated in vacuo and purified twice by silica gel chromatography using hexane/CH2CI2 (1 :0-1 .5:1) to yield Intermediate 50 as a white solid (605 mg, 15%).1H NMR (300MHz, DMSO-d5) oH. 9.95 (5, 1H), 7.78-7.91 (m, 1H), 7.61-7.73 (m, 1H), 6.97 (d, J=8.9 Hz, 1H), 6.50-6.59 (m, 1H), 1.54-1.70 (m, 9H).MS (E5) 311.9 (45%, [M-Hfl.

The synthetic route of 434958-85-7 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; KARUS THERAPEUTICS LTD; SHUTTLEWORTH, Stephen Joseph; SILVA, Franck Alexandre; CECIL, Alexander Richard Liam; ALEXANDER, Rikki Peter; GATLAND, Alice Elizabeth; FINNEMORE, Daniel John; (123 pag.)WO2017/29521; (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.6127-17-9,6-Chloro-2-methyl-1H-indole,as a common compound, the synthetic route is as follows.,6127-17-9

To a solution of 0.38 g (2.3 mmol) 6-chloro-2-methyl-1H-indole in 20 ml 1,2-dichloroethane at 0 C. were added 0.35 ml (2.5 mmol) trifluoroacetic anhydride. The reaction mixture was quenched with aqueous 2 M sodium carbonate solution after 30 min and extracted with dichloromethane (3*100 ml). The combined organic layers were dried over sodium sulfate and concentrated in vacuo to give the title compound (0.57 g; 95%) as an off-white solid. MS m/e (%): 260 (M-H+, 100).

As the paragraph descriping shows that 6127-17-9 is playing an increasingly important role.

Reference：
Patent; Bissantz, Caterina; Grundschober, Christophe; Masciadri, Raffaello; Ratni, Hasane; Rogers-Evans, Mark; Schnider, Patrick; US2008/161315; (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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.393553-57-6,6-Bromo-4-methoxy-1H-indole,as a common compound, the synthetic route is as follows.

To a solution of 6-bromo- 4-methoxy-lH-indole A.85 (2.117 g, 9.36 mmol) in DMF (46 mL) at room temperature was added Cs2CO3 (9.155 g, 28.1 mmol) followed by 4-chloropyrimidin-2-amine A.12 (1.456 g, 11.24 mmol) and the mixture was stirred at 80 0C for 21 hours. The mixture was poured into water (200 mL) and the aqueous layer was extracted with ethyl acetate (100 mL x 2). The combined organic layers were washed with brine (100 mL x 2), dried over Na2SO4, filtered, and concentrated under reduced pressure to give a brown solid. The product was purified by silica gel column chromatography using 65% ethyl acetate in hexane as eluent to give 4-(6- bromo-4-methoxy-lH-indol-l-yl)pyrimidin-2-amine A.134 (1.961 g, 65.6% yield) as an orange solid: 1H NMR (400 MHz, DMSO-d6) delta ppm 8.55 (1 H, s), 8.27 (1 H, d, J=5.9 Hz), 7.95 (1 H, d, J=4.0 Hz), 6.89 – 7.04 (4 H, m), 6.75 (1 H, d, J=3.7 Hz), 3.92 (3 H, s); Mass Spectrum (ESI) m/e = 319.0 [M+l (79Br)] and 321.0 [M+l (81Br)].

393553-57-6, 393553-57-6 6-Bromo-4-methoxy-1H-indole 24728034, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; AMGEN INC.; WO2009/158011; (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

6958-37-8,6958-37-8, 5-Nitro-1H-indole-3-carboxylic acid is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 5-nitroindole-3-carboxylic acid (2.45 g, 12 mmol) in methanol (50 cm3) was added sulphuric acid (1 cm3) and the solution stirred at reflux for 6 hours. The solution was allowed to cool and then poured onto ice-water, neutralised with sodium bicarbonate and the product filtered to give a yellow solid, which was recrystallised from methanol as an off-white solid. Yield 1.76 g, 67%. mp 282-2840C. deltaH 3.85 (3H, s, OCH3), 7.65 (IH, d, J 9, H7), 8.08 (IH, dd, Ji 9, J2 2.3, H6), 8.35 (IH, s, H2), 8.83 (IH, d, J 2.3, H4), 8.5 (IH, s, NH). uv lambdamax/nm 320 (15000), 251 (32450), lambdamin/nm 284, 213; pH 12 lambdamax/nm 366 (13100), 271 (31500), 213 (48100). m/z 243.1 (M+Na)+. Accurate mass measurement on (M+Na)+ Ci0H8N2O4Na 243.0396, deviation -5.73 ppm.

6958-37-8 5-Nitro-1H-indole-3-carboxylic acid 248136, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; MEDICAL RESEARCH COUNCIL; WO2007/135380; (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

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, Oxalyl chloride (1.55 mL, 18.3 mmol) was added to a suspensionof the above acid (2.48 g, 15.3 mmol) in DCM (100 mL, anhydrous)and DMF (0.05 mL, 0.64 mmol) at 20 C. The mixture wasstirred at 20 C for 1 h to give a colourless solution which wascooled to 0 C. N,O-Dimethylhydroxylamine hydrochloride (1.64g, 16.8 mmol) and pyridine (3.71 mL, 45.9 mmol) were addedsequentially and the mixture was stirred at 20 C for 18 h, thenpartitioned between EtOAc and sat. aq. NaHCO3. Column chromatographywith 95:5 DCM:EtOAc gave N-methoxy-N-methylbenzofuran-5-carboxamide (2.28 g, 73%) as a pale brown oil. 1H NMR(CDCl3) d 7.99 (d, J = 1.4 Hz, 1H), 7.65-7.69 (m, 2H), 7.52 (dt, J =8.6, 0.6 Hz, 1H), 6.82 (dd, J = 2.2, 0.9 Hz, 1H), 3.56 (s, 3H), 3.39 (s,3H). Found: [M+H] = 206.2.

90924-06-4 1-Methyl-4-indolecarboxylic Acid 14987287, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Article; Sutherland, Hamish S.; Tong, Amy S.T.; Choi, Peter J.; Conole, Daniel; Blaser, Adrian; Franzblau, Scott G.; Cooper, Christopher B.; Upton, Anna M.; Lotlikar, Manisha U.; Denny, William A.; Palmer, Brian D.; Bioorganic and Medicinal Chemistry; vol. 26; 8; (2018); p. 1797 – 1809;,
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.81779-27-3,4-Hydroxy-1H-indole-3-carbaldehyde,as a common compound, the synthetic route is as follows.,81779-27-3

EXAMPLE 2 OF REFERENCE 3-Formyl-4-hydroxyindole-1-carboxylic Acid tert-butyl Ester (2-1) (R7=R11=H) A mixture of the 3-formyl-4-hydroxyindole (1-1) 323 mg, di-tert-butyldicarbonate 458 mg, dimethylaminopyridine 12.5 mg and acetonitrile 25 ml was stirred under cooling in ice for 3 h.The solvent was removed under reduced pressure and the residue obtained was recrystallized from acetone-isopropyl ether to give the titled compound as pale yellow crystals, m.p. 159-161 C.(dec.), 389 mg.Yield 74%. 1H-NMR(CDCl3): 1.71 (9H, s), 6.84 (1H, dd, J=8.1, 0.9 Hz), 7.31 (1H, t, J=8.1 Hz), 7.61 (1H, dd, J=8.1, 0.9 Hz), 8.25 (1H, s), 9.76 (1H, d, J=0.6 Hz), 10.13 (1H, s).

81779-27-3 4-Hydroxy-1H-indole-3-carbaldehyde 9815282, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; Fukui, Yoshikazu; Adachi, Makoto; Sasatani, Takashi; US2003/236295; (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

20289-27-4, 7-(Benzyloxy)-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Furthermore, 7-benzyloxyindole (404 mg, 1.81 mmol) was hydrogenated over 10% palladium on carbon (40 mg) in EtOH (4.2 mL) at ambient temperature under atmosphere pressure for 6 h. The catalyst was filtered off and washed with EtOH. The filtrate was concentrated to give 7-hydroxyindole as pale purple crystals, which was rapidly and directly used for the next reaction., 20289-27-4

The synthetic route of 20289-27-4 has been constantly updated, and we look forward to future research findings.

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

14618-45-2, 3-(Trifluoroacetyl)indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of product of Step A (0.55 g, 2.58 mmol), K2CO3 (0.43 g, 3.1 1 mmol) and propyrgyl bromide (2 ml) in anhydrous DMF (8 ml), was stirred for 4 h. The mixture was quenched with NH4CI solution and diluted to 50 ml with EtOAc. The organic layer separated and washed with H2O, dried over MgSO4 and filtered. The filtrate was evaporated to give the title compound (0.57 g, 88%), as yellow crystalline material. 1H-NMR (CDCI3) 8.41 – 8.38 (b, 1 H); 7.99 (s, 1 H); 7.48 – 7.31 (m, 3H); 4.96 (d, 2H, J = 2.55 Hz); 2.58 (t, 1 H, J = 2.55 Hz).

14618-45-2, 14618-45-2 3-(Trifluoroacetyl)indole 589126, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; AKAAL PHARMA PTY LTD; GILL, Gurmit S; GROBELNY, Damian W; WO2010/43000; (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