Category: 183208-22-2

Related Products of 183208-22-2, 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.183208-22-2, name is 5-Bromo-1-methyl-1H-pyrrolo[2,3-b]pyridine, molecular formula is C8H7BrN2, molecular weight is 211.06, as common compound, the synthetic route is as follows.

To a solution of 5-bromo-1-methyl-1H-pyrrolo[2,3-bjpyridine (800 mg, 3.8 mmol) in MeOH (15 mL) were added Pd(dppf)C12 (272 mg, 0.38 mmol) and TEA (1.15 g, 11.4 mmol). The mixture was stirred at 80 C under CO (1 atm) overnight. The solvent was removed and the residue was purified by silica gel column (100-200 mush, PE/EA = 10/1) to give 1-methyl-1H-pyrrolo[2,3-bjpyridine-5-carboxylic acid methyl ester (665 mg, yield: 91%) as a yellow solid.?HNMR (300 MI-Tz, CDC13): = 9.00 (s, 1H), 8.57 (d, J= 1.2 Hz, 1H), 7.25 (d, J= 3.6 Hz, 1H), 6.55 (d, J 3.3 Hz, 1H), 3.96 (s, 3H), 3.92 (s, 3H). MS: m/z 191.0 (M+H).

The chemical industry reduces the impact on the environment during synthesis 183208-22-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; SANFORD-BURNHAM MEDICAL RESEARCH INSTITUTE; PINKERTON, Anthony, B.; HASSIG, Christian, A.; JACKSON, Michael, R.; ARDECKY, Robert, John; PASS, Ian; (436 pag.)WO2016/123392; (2016); A2;,
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.183208-22-2, name is 5-Bromo-1-methyl-1H-pyrrolo[2,3-b]pyridine, molecular formula is C8H7BrN2, molecular weight is 211.06, as common compound, the synthetic route is as follows.SDS of cas: 183208-22-2

To a solution of tert-butyl (S)-2-(methoxymethyl)pyrrolidine-1-carboxylate (663 mg, 3.08mmol) in DCM (10 mL) was added trifluoroacetic acid (1.76 g, 15.40 mmol) within 5 min at0C. The mixture was warmed up to room temperature within 2 h and carefully poured into a10% NaOH solution (60 mL). After extraction with DCM (2 × 50 mL) the combined organicphases were dried over MgSO4, and evaporated. The residue was dissolved in DCM (5 mL)and N,N-diisopropylethylamine (521 mg, 4.03 mmol) was added at room temperature. Thissolution containing the deprotected pyrrolidine was then stirred until it was needed.A two-neck flask was charged with 5-bromo-1-methyl-1H-pyrrolo[2,3-b]pyridine (3)(500 mg, 2.37 mmol) and dry THF (30 mL) under argon. The solution was cooled to -80 C inan ethanol/nitrogen cooling bath and t-BuLi (1.4 M in pentane, 1.69 mL, 2.37 mmol) wasS 6added dropwise. The reaction mixture was warmed up to -75 C within 10 min and transferredto a solution of DABCO-bis(sulfur dioxide) (569 mg, 2.37 mmol) in dry THF (15 mL) at -75C. The cooling bath was removed after 30 min and the reaction mixture warmed up to roomtemperature. The THF solvent was removed under reduced pressure and dry DCM (20 mL)was added. N-Chlorosuccinimide (379 mg, 2.84 mmol) was slowly added as a solution in dryDCM (5 mL) followed by dropwise addition of the deprotected pyrrolidine. After the additionof water (35 mL) the mixture was extracted with DCM (2 × 20 mL). The combined organicphases were dried over MgSO4, and evaporated. Column chromatographic purification (SiO2,CH/EtOAc, 2:1) yielded a colorless, crystalline solid [291 mg, 40% yield].MP: 66 – 67 C (CH/EtOAc).1H-NMR (300 MHz, CDCl3): delta = 1.50-1.60 (m, 2H, 13-CHa, 14-CHa), 1.79-1.89 (m, 2H,13-CHb, 14-CHb), 3.08-3.18 (m, 1H, 15-CHa), 3.34-3.42 (m, 1H, 16-CHa), 3.38 (s, 3H,18-CH3), 3.44-3.52 (m, 1H, 15-CHb), 3.68 (dd, 2JH,H = 9.2 Hz, 3JH,H = 3.8 Hz, 1H, 16-CHb),3.71-3.81 (m, 1H, 12-CH), 3.95 (s, 3H, C-19), 6.60 (d, 3JH,H = 3.5 Hz, 1H, 3-CH), 7.33 (d,3JH,H = 3.5 Hz, 1H, 2-CH), 8.39 (d, 4JH,H = 2.1 Hz, 1H, 4-CH), 8.80 (d, 4JH,H = 2.1 Hz, 1H,6-CH) ppm.13C-NMR (75 MHz, CDCl3): delta = 24.1 (t, C-14), 28.9 (t, C-13), 31.7 (q, C-19), 49.5 (t, C-15),59.1 (q, C-18), 59.3 (d, C-12), 75.3 (t, C-16), 101.2 (d, C-3), 119.7 (s, C-9), 125.7 (s, C-5),129.0 (d, C-2), 131.7 (d, C-4), 142.0 (d, C-6), 149.0 (s, C-8) ppm.ESI(+)-MS: calcd. for C14H19N3O3S + H+, 310.1220; found 310.1220.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,183208-22-2, 5-Bromo-1-methyl-1H-pyrrolo[2,3-b]pyridine, and friends who are interested can also refer to it.

Reference:
Article; Waldmann, Christopher M.; Hermann, Sven; Faust, Andreas; Riemann, Burkhard; Schober, Otmar; Schaefers, Michael; Haufe, Guenter; Kopka, Klaus; Bioorganic and Medicinal Chemistry; vol. 23; 17; (2015); p. 5734 – 5739;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 183208-22-2, 5-Bromo-1-methyl-1H-pyrrolo[2,3-b]pyridine, 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, 183208-22-2, blongs to pyridine-derivatives compound. SDS of cas: 183208-22-2

[0654] To a stirred solution of 5-bromo-1-methyl-1H-pyrrolo [2, 3-bj pyridine (350 mg, 3 mmol) in 1,4-dioxane: water (4:1, 2.5 mL) at room temperature under an argon atmosphere were added lithium hydroxide (445 mg, 10 mmol), cyclopropylboronic acid (455 mg, 5 mmol) and Pd(dppf)2C12 (193 mg, 0.26 mmol). The reaction mixture was stirred at 120 C for 4 h in a sealed tube. After consumption of starting material (by TLC), the reaction mixture was filtered, the filtrate was diluted with water (20 mL) and extracted with EtOAc (2 x 20 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by column chromatography using 10- 20% EtOAc: Hexane to afford 5-cyclopropyl-1-methyl-1H-pyrrolo [2, 3-bj pyridine (120 mg, 26%) as colorless liquid. ?H NMR (CDC13,. 400 MHz): 8.20 (s, 1H), 7.56 (s, 1H), 7.13 (d, 1H), 6.36 (d, 1H), 3.87 (s, 3H), 2.05-2.02 (m, 1H), 1.00-0.94 (m, 2H), 0.73-0.68 (m, 2H); LCMS: 62.8%; 172.8 (M+1); (column; Ascentis Express C-18 (50 x 3.0 mm, 2.7 jtm); RT 1.97 mm; mobile phase: 0.025% Aq TFA+5% ACN: ACN+5% 0.025% Aq TFA; T/B%:0.01/5, 0.5/5, 3/100, 5/100; flow rate: 1.2 mL/min) (Gradient); TLC: 20% EtOAc/ Hexane (R1: 0.5).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,183208-22-2, its application will become more common.

Reference:
Patent; FORUM PHARMACEUTICALS INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; HARRISON, Bryce, Alden; (273 pag.)WO2017/31325; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem