Month: September 2020

348640-06-2, 4-Bromo-7-azaindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine A mixture of 4-bromo-1H-pyrrolo[2,3-b]pyridine (10.0 g, 51.0 mmol), Pin2B2 (15.5 g, 61.0 mmol), PdCl2(dppf) (2.0 g, 2.5 mmol) and KOAc (10.0 g, 102 mmol) in 1,4-dioxane (200 mL) was degassed with Ar for 5 minutes. The reaction mixture was heated to 80 C. and stirred for 16 h. The mixture was cooled to RT, filtered through CELITE and concentrated under reduced pressure. The residue was purified via silica gel chromatography (0-25% EtOAc in hexanes) to afford the title compound (3.8 g, 31% yield) as a white solid. MS (ES+) C13H17BN2O2 requires: 244, found: 245 [M+H]+., 348640-06-2

The synthetic route of 348640-06-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Board of Regents, The University of Texas System; DI FRANCESCO, Maria Emilia; JONES, Philip; CARROLL, Christopher Lawrence; CROSS, Jason Bryant; RAMASWAMY, Suyambu Kesava Vijayan; JOHNSON, Michael Garrett; LIVELY, Sarah; LAPOINTE, David; US2019/16713; (2019); 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.858515-65-8,4-Methyl-1H-indole-3-carboxylic acid,as a common compound, the synthetic route is as follows.

858515-65-8, A procedure for converting quinuclidin-4-ylmethyl 4-methyl-l//-indole-3-carboxylate phosphate salt (93% assay purity; mix of polymorphs) to quinuclidin-4-ylmethyl 4-methyl-lH- indole-3-carboxylate phosphate salt (polymorphic Form A) is shown in Scheme 1. step 1: A solution of 4-methyl-lH-indole-3-carboxylic acid (1.88 kg) in DMF (0.54 kg) I was added to DCM (63 kg) in a reactor. The system was vacuumed and refilled with N2 for three cycles. The solution was heated to 25-35 C (internal temperature). Oxalyl chloride (2.7 kg) Lambda was added drop-wise over 2 hr while maintaining the temperature at 25-35 C under nitrogen. The mixture was stirred for 4 hrs at 25-35 C under nitrogen. The reaction mixture was concentrated under vacuum (0.08 Mpa) at 30-35 C to about 15-20 L and evaporated at 35 ¡À 5 C using a rotary evaporator to remove DCM and oxalyl chloride until an obvious distillate was observed. The reaction mixture was charged with DCM (15.0 kg) and evaporated to dryness, and this charge-evaporate procedure was repeated for two cycles. Fifteen kilograms of DCM was charged to the mixture and stirred to obtain a clear solution, and an additional 15 kg of DCM was charged to the mixture in the rotary evaporator. The solution in the rotary evaporator was transferred to a dropping tank under nitrogen. Quinuclidin-4-ylmethanol N-borane complex (1.5 kg) and Et3N (1.65 kg) were added to a reactor containing DCM (15.0 kg). The mixture was cooled to 0-5 C (internal temperature), and the solution from the dropping tank in the previous step was added over 2 hrs under nitrogen at 0-5 C. The mixture was heated to 15-25 C with stirring and was stirred at 15- 25 C for 16 hrs under nitrogen. Saturated NH4CI solution (20.3 kg) was added dropwise to quench this reaction at 15-25 C. The mixture was stirred for 30 min and settled aside for 15 min. The organic layer was separated and washed with brine (40.8 kg) and dried with anhydrous Na2SC4 (3.0 kg). The solid was filtered, and the cake was washed with DCM (3.0 kg).

The synthetic route of 858515-65-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ALPHARMAGEN, LLC; NG, John, Sau-Hoi; NG, Raymond; (86 pag.)WO2017/120532; (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.2591-98-2,2-(1H-Indol-3-yl)acetaldehyde,as a common compound, the synthetic route is as follows.

At O0C under argon, lithium aluminum hydride (14 mg, 0.00036 mol) was added to a solution of intermediate 7 (74 mg, 0.00036 mol) in THF (1 ml). The mixture was stirred at 0C for 1 hour, quenched with a 5% solution of potassium hydrogen sulfate, and extracted twice with EtOAc. The organic layer was separated, washed with brine, dried (MgSO4), filtered, and the solvent was evaporated, to give the indole-3-yl acetaldehyde as an orange oil. A mixture of intermediate 9 (200 mg, 0.00074 mol) and sodium cyanoborohydride (64 mg, 0.0010 mol) in MeOH (2.3 ml) and acetic acid (2 drops) was added dropwise to a solution of the previous aldehyde (236 mg, 0.0015 mol) in MeOH (2 ml). The reaction mixture was stirred at room temperature for 16 hours. The reaction was quenched with water, made alkaline with a saturated solution of sodium hydrogen carbonate and extracted 3 times with EtOAc. The organic layer was separated, washed with brine, dried (MgSO4), filtered, and the solvent was evaporated. The residue was purified by column chromatography over silica gel (40-63 mum) (eluent: EtOAc/MeOH 100/0 to 90/10). The pure fractions were collected and the solvent was evaporated, yielding 190 mg (44 %) of compound 3 as an orange foam.1H NMR (300 MHz, CDCl3) delta 8.42 (d, IH, J=5.7), 8.08 (brs, IH), 7.79 (d, IH, J=2.4), 7.63 (d, IH, J=7.8), 7.40 (d, IH, J=8.1), 7.25-7.07 (m, 5H), 6.59 (s, IH), 6.48 (dd, IH, J=8.7. J=2.1), 4.00 (m, 5H), 3.48 (t, 2H, J=6.8), 3.12 (m, 4H). MS (ES+) w/z 413 (M+l).

2591-98-2, As the paragraph descriping shows that 2591-98-2 is playing an increasingly important role.

Reference£º
Patent; JANSSEN PHARMACEUTICA N.V.; WO2007/107545; (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

16732-64-2, 4-Bromo-1H-indole-2-carboxylic acid is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

a) 4- (2-Ethylphenyl)-indole-2-carboxylic acid; To a mixture of 0.28 g of 4-bromo-indole-2-carboxylic acid and 0.069 g of tetrakistriphenylphosphinepalladium in 11 ml of toluene and 2 ml of 2M soda is added a solution of 0.300 g of 2-ethylphenylboronic acid in 3 ml of ethanol. This mixture is refluxed for 16 h, filtered and the aqueous phase acidified with 2N HCI and extracted with ethyl acetate. Concentration of the organic phase gives the product as a brownish powder, m. p. 230-233, sufficiently pure for the next step.

16732-64-2, The synthetic route of 16732-64-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2005/70886; (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

3468-17-5, (1H-Indol-6-yl)methanamine is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 76: Preparation of N-((lH-indol-6-yl)methyl)-5-(4-((2-oxopyridin-l(2H)- yl)methyl)benzyl)nicotinamide A mixture of 5-(4-((2-oxopyridin-l(2H)-yl)methyl)benzyl)nicotinic acid (91 mg, 0.28 mmol, 1.0 eq.), (1H- indol-6-yl)methanamine (44 mg, 0.30 mmol, 1.07 eq.), HATU (114 mg, 0.3 mmol, 1.07 eq.) and DIPEA (0.5 mL) in DCM (3 mL) was stirred at rt overnight. Filtered and the solid was collected and triturated with water to afford N-((lH-indol-6-yl)methyl)-5-(4-((2-oxopyridin-l(2H)-yl)methyl)benzyl)nicotinamide as a white solid (100 mg, 78.7%). LRMS (M+H+) m/z calculated 449.2, found 449.2. NMR (CD3OD, 400 MHz) delta 8.85 (s, 1 H), 8.57 (s, 1 H), 8.09 (s, 1 H), 7.69 (d, 1 H), 7.55-7.51 (m, 2 H), 7.39 (t, 1 H), 7.29-7.22 (m, 5 H), 7.03 (d, 1 H), 6.57 (d, 1 H), 6.43-6.37 (m, 2 H), 5.18 (s, 2 H), 4.67 (s, 2 H), 4.08 (s, 2 H).

3468-17-5, As the paragraph descriping shows that 3468-17-5 is playing an increasingly important role.

Reference£º
Patent; LIFESCI PHARMACEUTICALS, INC.; MCDONALD, Andrew; WO2015/103317; (2015); 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.885520-70-7,4-Bromo-6-fluoro-1H-indole,as a common compound, the synthetic route is as follows.

885520-70-7, To a solution of 4-bromo-6-fluoro-lH-indole (6.0 g, 25.53 mmol) and bis(pinacolato)diboron (9.7 g, 38.19 mmol) in anhydrous DMSO (120 mL) were added KOAc (7.5 g, 76.41 mmol) and [l,r-bis(diphenylphosphine)ferrocene]-dichloropalladium (1.0 g, 1.22 mmol). The mixture was heated at 80 ¡ãC for 18 h. The reaction mixture was cooled to RT and partioned between EtOAc and H2O. The organic layer was washed successively with H2O and brine, dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (silica gel, pentane:EtOAc 75:25) to provide the title compound as a white solid (4.6 g, 61 percent).NMR deltaH (300 MHz, CDCl3) 1.39 (s, 12H), 7.02 (m, IH), 7.14-7.19 (m, IH), 7.20-7.26 (m, IH), 7.38 (dd, J = 2.4, 9.9, IH) and 8.16 (s, IH).

As the paragraph descriping shows that 885520-70-7 is playing an increasingly important role.

Reference£º
Patent; F.HOFFMANN-LA ROCHE AG; WO2008/152390; (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.93247-78-0,Methyl 1H-indole-7-carboxylate,as a common compound, the synthetic route is as follows.,93247-78-0

Example 17; Preparation of Al3; Indole-7 carboxyldehyde (K-44); Methyl 7-indolecarboxylate was prepared according to literature procedure {Batcho B. and Leimgruber, K., Org. Syn. VoI HV, page 34-40). To a solution of methyl 7-indolecarboxylate (13 g, 74.2 mmol) in anhydrous THF (250 niL) was added LiAlH4 (10.9 g, 0.288 mol) in portions, and reaction mixture was heated to reflux for 2h. After cooling to room temperature, the excess hydride was quenched by addition of water (12mL), 15% NaOH (12mL) and water (26mL). The solids were removed by filtration through a pad of Celite and filtrate was evaporated in vacuo to yield (lH-indol-7-yl)- methanol (10.7 g, 98%). 1HNMR (CDCl3). To a solution of the alcohol, (IH- indol-7-yl)-methanol (8.0 g, 54.3 mmol) in 400 mL of methylene chloride was added activated manganese (IV) oxide (85%, 41.0 g, 0.40 mol), and stirred at ambient temperature for 72h. After additional of 200 mL of methylene chloride and 400 mL of methanol to the reaction mixture, the whole mixture was filtered through a pad of silica gel to remove solid materials. The filtrate was concentrated to afford a crude product, which was purified by a column chromatography on silica gel to yield lH-indole-7-carbaldehyde, K-44 (6.55 g, 83%).

The synthetic route of 93247-78-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; DECODE CHEMISTRY, INC.; WO2006/44415; (2006); 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

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

General procedure: Compound 2 (5 mmol) was added to hydrazine- hydrate (80) (3 mL)at room temperature, and the mixture was irradiated continually for 5-8 min at 300 W. The reaction progress was monitored by TLC. After the reaction was complete and the mixture was sufficiently cooled, intermediate 3 (yield 83-98) was formed., 50820-65-0

50820-65-0 Methyl 1H-indole-6-carboxylate 639844, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Article; Ye, Ying; Suo, Yourui; Yang, Fang; Yang, Yongjing; Han, Lijuan; Journal of Chemical Research; vol. 39; 5; (2015); p. 296 – 299;,
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

221352-46-1, 2-(tert-Butoxycarbonyl)isoindoline-1-carboxylic acid is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution ofHATU (1.83 g, 4.82 mmol) in DMF (15 mL) was added Hunig’s base(2.34 mL, 13.1 mmol). After stirring for 5 min, racemic 2-(tert-butoxycarbonyl)isoindoline-1-carboxylic acid 2-1 (1.15 g, 4.38 mmol) and ammonium chloride (1.41 g, 26.3 mmol) wereadded to the mixture. The reaction was stirred at room temperature for 18 h. The reaction waspartitioned between EtOAc (20 mL) and water (20 mL). The layers were separated and theaqueous layer was extracted with EtOAc (2 x 20 mL). The combined organic layer waswashed with brine, dried over MgS04, filtered and concentrated. The residue was purified by silica gel chromatography (IS CO 120 g column) eluting with a hexanes/EtOAc gradient (0 to100% EtOAc) to afford the title compound. LRMS mlz (M+H) 263.2 found, 263.1 required., 221352-46-1

The synthetic route of 221352-46-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; MERCK SHARP & DOHME CORP.; GRESHOCK, Thomas, J.; MULHEARN, James, J.; ROECKER, Anthony, J.; JIAN, Tianying; ZHOU, Gang; GUO, Liangqin; WON, Walter; ZHANG, Ting; ANAND, Rajan; STELMACH, John, E.; WANG, Deping; KIM, Ronald, M.; LAYTON, Mark, E.; BURGEY, Christopher, S.; NANTERMET, Philippe, G.; (129 pag.)WO2018/93694; (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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.110543-98-1,Ethyl 5-acetoxy-6-bromo-2-(bromomethyl)-1-methyl-1H-indole-3-carboxylate,as a common compound, the synthetic route is as follows.

Thiophenoi (99.8 pL, 0.972 rnol, 1 .0 eq.) was added to a solution of potassium hydroxide (164 mg, 2,92 -mmol, 3.0 eq.) in methanol {2 ml) and left to stir at room temperature for 15 min. Afte this time, the solution was cooled on ice and bromo indole 2 (880 nig, 0,972 mmol, 10 eq.) in CH2.CJ2 (5 mL) was added. The reaction was left to stir for 3 h before neutralisation with acetic acid. The solvent was removed in vacuo and columned directly (20% EiOAc in petrol) to yield the title product as a pale yellow solid {362 mg, 86%). UUR deltaEta (600 MHz, CDCb) 7.74 (s, 1 H , Hr), 7.43 (s, 1H, H4), 7.36 (dq, J – 5.2, 3.4, 2.4 Hz, 2H, Hw), 7.25 110543-98-1

As the paragraph descriping shows that 110543-98-1 is playing an increasingly important role.

Reference£º
Patent; THE SCRIPPS RESEARCH INSTITUTE; WILSON, Ian, A.; WOLAN, Dennis, W.; WRIGHT, Zoe, V, .F.; KADAM, Rameshwar, U.; WU, Nicholas, C.; (28 pag.)WO2018/112128; (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