Downstream synthetic route of 40913-43-7

40913-43-7 1-Ethyl-1H-indole-2-carbaldehyde 13693148, aindole-building-block compound, is more and more widely used in various fields.

40913-43-7, 1-Ethyl-1H-indole-2-carbaldehyde is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,40913-43-7

In two equal batches, 1,1 -dimethyl ethyl {(3R)-l-[(4-{[3-({[(9H-fluoren-9- ylmethyl)oxy]carbonyl}amino)propyl]amino}-3-nitrophenyl)carbonyl]-3- piperidinyl} carbamate (6 g, 9.32 mmol), l-ethyl-lH-indole-2-carbaldehyde (7.844 g, 27.96 mmol) and sodium hydrosulfite (4.868 g, 27.96 mmol) were combined in ethanol (40 mL) and water (20 mL) and heated in a Biotage Initiator microwave using initial high absorbtion setting to 100 C for 6 h. The reaction mixtures were combined and then partitioned between DCM (150 mL) and water (150 mL). The ethanol from the reaction mixture led to poor separation of the two layers, so the whole mixture was evaporated under vacuum – to the point where it was assumed most of the ethanol had evaporated and only the aqueous layer remained. The aqueous layer was then extracted with DCM (3 x 100 mL). The organics were combined, dried using a hydrophobic frit and evaporated under vacuum. The sample was loaded in dichlorom ethane and purified by Biotage SP4 (2 x SNAP 100 g silica) using a gradient of 50-100% cyclohexane-ethyl acetate. The appropriate fractions were combined and evaporated under vacuum to give the required product 1, 1 -dimethyl ethyl [(3R)-l-({2-(l- ethyl- 1 H-indol-2-yl)- 1 – [3 -( { [(9H-fluoren-9-ylmethyl)oxy] carbonyl } amino)propyl] – 1 H- benzimidazol-5-yl}carbonyl)-3-piperidinyl]carbamate (1.83 g, 2.386 mmol, 51.2 % yield) as an off- white foam.LCMS (Method B): Rt 1.37 min, MH+ 767.

40913-43-7 1-Ethyl-1H-indole-2-carbaldehyde 13693148, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; AMANS, Dominique; ATKINSON, Stephen, John; BARKER, Michael, David; CAMPBELL, Matthew; DIALLO, Hawa; DOUAULT, Clement; GARTON, Neil, Stuart; LIDDLE, John; RENAUX, Jessica, Fanny; SHEPPARD, Robert, John; WALKER, Ann, Louise; WELLAWAY, Christopher, Roland; WILSON, David, Matthew; (284 pag.)WO2016/185279; (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

Analyzing the synthesis route of 40913-43-7

40913-43-7, As the paragraph descriping shows that 40913-43-7 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.40913-43-7,1-Ethyl-1H-indole-2-carbaldehyde,as a common compound, the synthetic route is as follows.

Intermediate 2 l-Ethyl-3-fluoro-l//-indole-2-carbaldehydeA 50 mL round bottom flask was charged with 1 -ethyl- 1 H- indole-2-carbaldehyde (Intermediate 1, 524 mg, 3.03 mmol) and Selectfluor (1.29 g, 3.64 mmol). MeCN (6.0 mL) was added, and the mixture was allowed to stir at room temperature. After 90 min, the solvent was removed in vacuo, and the residue was partitioned between EtOAc and H2O, and the aqueous layer was further extracted with EtOAc. The combined organic layers were washed with brine, dried (MgSO4), filtered, and concentrated. The crude material was purified by silica gel chromatography (gradient elution; Rf in 95:5 hexanes:EtOAc = 0.42) to give a colorless solid (191 mg, 33%) of 90% purity (remainder is unreacted starting material). 1H NMR (400 MHz, CDCl3) delta 1.31 – 1.39 (m, 3 H) 4.52 (q, J=7.07 Hz, 2 H) 7.16 (m, 1 H) 7.34 (m, 1 H) 7.38 – 7.45 (m, 1 H) 7.70 (m, 1 H) 10.08 (s, 1 H). M/Z 191.

40913-43-7, As the paragraph descriping shows that 40913-43-7 is playing an increasingly important role.

Reference£º
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2008/59238; (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

Brief introduction of 40913-43-7

As the paragraph descriping shows that 40913-43-7 is playing an increasingly important role.

40913-43-7, 1-Ethyl-1H-indole-2-carbaldehyde is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,40913-43-7

In two equal batches, 1,1 -dimethyl ethyl {(3R)-l-[(4-{[3-({[(9H-fluoren-9- ylmethyl)oxy]carbonyl}amino)propyl]amino}-3-nitrophenyl)carbonyl]-3- piperidinyl} carbamate (6 g, 9.32 mmol), l-ethyl-lH-indole-2-carbaldehyde (7.844 g, 27.96 mmol) and sodium hydrosulfite (4.868 g, 27.96 mmol) were combined in ethanol (40 mL) and water (20 mL) and heated in a Biotage Initiator microwave using initial high absorbtion setting to 100 C for 6 h. The reaction mixtures were combined and then partitioned between DCM (150 mL) and water (150 mL). The ethanol from the reaction mixture led to poor separation of the two layers, so the whole mixture was evaporated under vacuum – to the point where it was assumed most of the ethanol had evaporated and only the aqueous layer remained. The aqueous layer was then extracted with DCM (3 x 100 mL). The organics were combined, dried using a hydrophobic frit and evaporated under vacuum. The sample was loaded in dichlorom ethane and purified by Biotage SP4 (2 x SNAP 100 g silica) using a gradient of 50-100% cyclohexane-ethyl acetate. The appropriate fractions were combined and evaporated under vacuum to give the required product 1, 1 -dimethyl ethyl [(3R)-l-({2-(l- ethyl- 1 H-indol-2-yl)- 1 – [3 -( { [(9H-fluoren-9-ylmethyl)oxy] carbonyl } amino)propyl] – 1 H- benzimidazol-5-yl}carbonyl)-3-piperidinyl]carbamate (1.83 g, 2.386 mmol, 51.2 % yield) as an off- white foam.LCMS (Method B): Rt 1.37 min, MH+ 767.

As the paragraph descriping shows that 40913-43-7 is playing an increasingly important role.

Reference£º
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; AMANS, Dominique; ATKINSON, Stephen, John; BARKER, Michael, David; CAMPBELL, Matthew; DIALLO, Hawa; DOUAULT, Clement; GARTON, Neil, Stuart; LIDDLE, John; RENAUX, Jessica, Fanny; SHEPPARD, Robert, John; WALKER, Ann, Louise; WELLAWAY, Christopher, Roland; WILSON, David, Matthew; (284 pag.)WO2016/185279; (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