Simple exploration of 4-Bromo-1H-indole-2-carboxylic acid

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Chemistry is the experimental and theoretical study of materials on their properties at both the macroscopic and microscopic levels.In a patent, Quality Control of: 4-Bromo-1H-indole-2-carboxylic acid, Which mentioned a new discovery about 16732-64-2

A compound of formula (I) or a pharmaceutically acceptable salt or prodrug ester thereof, wherein the variants R, R9, Z, X, Q and Y are defined in the specification.

I hope this article can help some friends in scientific research. I am very proud of our efforts over the past few months and hope to 16732-64-2, help many people in the next few years.Computed Properties of C9H6BrNO2

Reference:
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 16732-64-2

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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.16732-64-2,4-Bromo-1H-indole-2-carboxylic acid,as a common compound, the synthetic route is as follows.

Intermediate 115: 4-Bromo-lH-indole-2-carboxamide (0796) To a suspension of 4-bromo-l indole-2-carboxylic acid (0.276 mL, 2.12 mmol, commercially available from, for example, Ark Pharm) in dichloromethane (15 mL) was added oxalyl chloride (0.220 mL, 2.51 mmol). The suspension was stirred at rt for approx. 3 days in total. During this time, DMF (0.020 mL, 0.26 mmol) was added after 5.5 h. Further oxalyl chloride (0.100 mL, 1.14 mmol) was added after 23.75 h. Further oxalyl chloride (0.100 mL, 1.142 mmol) was added after 27.15 h. The reaction mixture was left to stir over the weekend, during which time the solvent had evaporated to give a sticky light brown solid. This was redissolved in dichloromethane (15 mL) and to this solution was added oxalyl chloride (0.100 mL, 1.14 mmol) and DMF (0.020 mL, 0.26 mmol). The resulting solution was stirred for a further 2 h 45 min to afford a brown solution. This solution was added dropwise to a stirring solution of ammonia (35% in water) (10 mL, 162 mmol) and ice (approx. 10 g) and the resulting mixture left to stand for approx. 3 h. To this was added ethyl acetate (10 mL) and water (10 mL) and the layers separated. To the aqueous layer was added brine (approx. 5 mL) and this was extracted with further ethyl acetate (3 x 30 mL). The organic layers, which contained a brown precipitate, were combined and evaporated in vacuo o give a brown solid. This was transferred in methanol (approx. 10 mL) and this emulsion evaporated in vacuoto give a brown solid. This solid was triturated with dichloromethane (approx. 3 x 20 mL) and the supernatant filtered. The filtrate was concentrated to approx. 10 mL, directly applied to the top of a 50 g SNAP cartridge and purified by flash column chromatography. The column was eluted with a gradient of 20% – 70% ethyl acetate in cyclohexane. The required fractions were evaporated in vacuo to give 4-bromo-l indole-2- carboxamide (95.0 mg, 0.40 mmol, 19 % yield) as an off-white solid. (0797) LCMS (2 min High pH): Rt = 0.87 min, [M-H]- = 237.1.

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; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; ATKINSON, Stephen John; DEMONT, Emmanuel Hubert; HARRISON, Lee Andrew; LEVERNIER, Etienne; PRESTON, Alexander G; SEAL, Jonathan Thomas; WALL, Ian David; WATSON, Robert J; WOOLVEN, James Michael; (225 pag.)WO2017/174621; (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

Analyzing the synthesis route of 16732-64-2

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

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

Some tips on 16732-64-2

16732-64-2, 16732-64-2 4-Bromo-1H-indole-2-carboxylic acid 4042604, aindole-building-block compound, is more and more widely used in various.

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

Intermediate Cl : 4-Bromo-l -methyl- lH-indole-2-carboxylic acidTo a solution of 4-bromo-lH-indole-2-carboxylic acid (514 mg, 2.14 mmol) in DMF (16 mL), dimethyl carbonate (4.5 mL, 53.4 mmol) and DABCO (25 mg, 0.214 mmol) was added, and the solution was heated to 12O0C for 7 hours. The reaction was diluted with EtOAc, and the organics were washed with H2O (2x), IN HCl (Ix), and brine (Ix). The organics were dried over Na2SO4, filtered, concentrated, and the resulting residue was purified on SiO2 (gradient elution, 15-40% EtOAc/hexanes) to yield the intermediate ester as a white solid. MeOH (3 mL), H2O (1.5 mL) and LiOH monohydrate (3 eq.) were added to a solution of the ester in THF (3 mL), and left to stir for 16 hours. The reaction mixture was concentrated, and the residue was partitioned between EtOAc and IN HCl, and extracted with EtOAc (2x). The organics were combined, washed with brine (Ix), dried over Na2SO4, filtered, and concentrated to yield the title compound as a white solid. LRMS (M+H)+ Calcd. = 254; found 254.

16732-64-2, 16732-64-2 4-Bromo-1H-indole-2-carboxylic acid 4042604, aindole-building-block compound, is more and more widely used in various.

Reference£º
Patent; MERCK & CO., INC.; ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P. ANGELETTI S.P.A.; WO2008/57209; (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

Downstream synthetic route of 16732-64-2

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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.16732-64-2,4-Bromo-1H-indole-2-carboxylic acid,as a common compound, the synthetic route is as follows.

To a solution of compound 1 (0.36 g, 1.49 mmol, 1 eq) and compound 1A (366.33 mg, 1.49 mmol, 1 eq) in DMF (10 mL) was added HATU (851.82 mg, 2.24 mmol, 1.5 eq), DIEA (579.07 mg, 4.48 mmol, 780.41 uL, 3 eq) stirred at 15C for 16 hrs. LCMS showed the starting material was consumed and the desired MS was detected. The reaction was triturated with water (20 mL) and filtered. The filter cake was triturated with EtOAc (20 mL) and filtered. The filter cake was concentrated to give compound 2 (0.5 g, 1.07 mmol, 71.64% yield) as a yellow solid, which was confirmed. The residue was used directly next step without purification. LCMS: RT = 1.345 min, MS cal.: 467.32, [M+H] + = 468.7. 1H NMR (400MHz, DMSO-d6) d ppm 12.06 (s, 1H), 9.23 (s, 1H), 7.54 – 7.44 (m, 3H), 7.43 – 7.36 (m, 3H), 7.30 (d, J = 6.8 Hz, 1H), 7.17 – 7.10 (m, 1H), 6.72 (d, J = 2.0 Hz, 1H), 4.38 – 4.20 (m, 2H), 3.57 (br s, 2H), 2.14 – 1.96 (m, 2H), 1.89 (br d, J = 13.2 Hz, 2H).

As the paragraph descriping shows that 16732-64-2 is playing an increasingly important role.

Reference£º
Patent; KLEO PHARMACEUTICALS, INC.; BUNIN, Anna; IBEN, Lawrence G.; MANION, Douglas; SPIEGEL, David Adam; WELSCH, Matthew Ernest; (397 pag.)WO2019/136442; (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