Category: 916325-85-4

Synthetic Route of 916325-85-4 , The common heterocyclic compound, 916325-85-4, name is 5-Bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid, molecular formula is C7H4BrN3O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

Compound Ic (1.0 g, 4.13 mrnol) and 3-(t°7?-butyl-dimethyl-si]anyloxymethyl)- benzene-l,2-diamine Compound 6a (1.05 g, 4.17 mmol), HATU (1.58 g, 4.16 mmol) EPO and DIPEA (2.5 mL, 35.9 mmol) in DMF (50 mL) was stirred at room temperature overnight. The solvent was removed and the residue was dissolved in ethyl acetate (100 mL), then sequentially washed with hydrochloric acid (20 mL, IM), water (30 mL x 3) and brine (20 mL). The organic solution was evaporated to dryness, in vacuo and purified by silica gel chromatography (10% to 50% of ethyl acetate in hexanes) to yield 5-bromo-lH-pyrazolo[3,4-b]pyridine-3-carboxylic acid [2-amino-3-(tert-butyl- dimethyl-silanyloxymethyl)-phenyl]-amide Compound 6b (1.21g, 61% yield) as a yellow powder. 1H NMR (300 MHz, CDCl3) delta 8.91 (d, IH, J = 2.1 Hz), 8.73 (s, IH), 8.67 (d, IH, 7 = 2.1 Hz), 7.47 (d, IH, 7 = 7.2 Hz), 7.01 (d, IH, 7 = 7.2 Hz), 6.83 (t, IH, J = 7.2 Hz), 4.78 (s, 2H), 0.95 (s, 9H), 0.11 (s, 6H); MS (ESI) m/z: 477 (M+H+).

The synthetic route of 916325-85-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA, N.V.; WO2006/130673; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 916325-85-4, 5-Bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, Computed Properties of C7H4BrN3O2, blongs to pyridine-derivatives compound. Computed Properties of C7H4BrN3O2

To a solution of 5-bromo-1H-pyrazole[3,4-b]pyridine-3-carboxylic acid (XVIII) (0.242 g, 1 mmol) in dry DMF (5 mL) was added CDI (0.178 g, 1.1 mmol) and heated for 3 h at 65 C. under nitrogen. The solution was cooled to room temperature and N,O-dimethyl hydroxylamine hydrochloride (0.107 g, 1.1 mmol) was added to the solution. The solution was again heated for 3 h at 65 C. under nitrogen. The solution was cooled and the solvent was evaporated under reduced pressure. The residue was dissolved in DCM, washed successively with a 10% HCl solution, a saturated aqueous NaHCO3 solution and brine. The organic phase was dried over MgSO4, filtered and concentrated under reduced pressure to produce 5-bromo-N-methoxy-N-methyl-1H-pyrazolo[3,4-b]pyridine-3-carboxamide (XIX) as a white solid (260 mg, 0.91 mmol, 92% yield). 1H NMR (CDCl3) delta ppm 3.55 (s, 3H), 3.78 (s, 3H), 8.59 (d, J=3.01 Hz, 1H), 8.67 (d, J=3.01 Hz, 1H); ESIMS found for C9H9BrN4O2 m/z 285.4 (M+H).

The synthetic route of 916325-85-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Samumed, LLC; Hood, John; Kumar KC, Sunil; Wallace, David Mark; US2013/296302; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.916325-85-4, name is 5-Bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid, molecular formula is C7H4BrN3O2, molecular weight is 242.03, as common compound, the synthetic route is as follows.name: 5-Bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid

To a solution of 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid (XXXIV) (1.6 Kg, 6.6 mol) in anhydrous MeOH (32 L) was added H2SO4 (160 mL). The reaction was slowly heated to 70oC and stirred for 20 hours. The solution was concentrated under vacuum to a volume of 1.6 L. The residue was partitioned between DCM (120 L) and aqueous 10% NaHCO3 (32 L). The organic phase was separated and washed with aqueous 25% NaCl (32 L), dried over Na2SO4 and concentrated to a volume of 4.8 L. The product was crystallized by charging the solution with 3 x n-heptane (8 L) while concentrating the volume to 4.8 L after each addition of n- heptane. The solid was filtered and dried under vacuum at 50oC to produce methyl 5-bromo-1H- pyrazolo[3,4-b]pyridine-3-carboxylate (XXXV) (1.53 Kg, 6.0 mol, 80.6% purity, 90.4% assay yield).1H NMR (DMSO-d6, 400 MHz) d ppm 3.95 (s, 3H), 8.62 (d, J=2Hz, 1H), 8.73 (d, J=2.4Hz, 1H), 14.78 (brs, 1H); ESIMS found C8H6BrN3O2 m/z 256.0 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,916325-85-4, 5-Bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; SAMUMED, LLC; KC, Sunil Kumar; MITTAPALLI, Gopi Kumar; CHIRUTA, Chandramouli; HOFILENA, Brian Joseph; (128 pag.)WO2019/241540; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem