Category: 84539-30-0

Synthetic Route of 84539-30-0, 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.84539-30-0, name is 5-Bromo-N-methylpyridin-2-amine, molecular formula is C6H7BrN2, molecular weight is 187.04, as common compound, the synthetic route is as follows.

To a microwave reaction vial was added N-(5-fert- butylisoxazol-3-yl)-2-(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)phenyl)acetamide from Step 1 of Example 85 (350 mg, 0.91 mmol), 5-bromo-N- methylpyridin-2-amine (256 mg, 1.37 mmol), 2M aq sodium carbonate (1.37 mL, 2.73 mmol), acetonitrile (10 mL), and [1,1′- bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct (74.3 mg, 0.091 mmol). The vial was purged with argon, sealed, and heated in a microwave reactor at 150 C for 15 min. The mixture was partitioned between EtOAc (50 mL) and water (50 mL), and the aqueous layer was separated and extracted with EtOAc (2 x 40 mL). The combined organic layers were washed with brine (2 ^ 30 mL), dried over MgS04, filtered and concentrated under reduced pressure. The crude product was purified by silica gel chromatography, eluting with 0 – 70% EtOAc in hexanes to give N-(5-tert-butylisoxazol-3-yl)-2-(4-(6-(methylamino)pyridin-3- yl)phenyl)acetamide (165 mg, 50%) as an off-white solid. 1H NMR (300 MHz, DMSO-t/6) 6 11.20 (s, 1H), 8.30 (d, J= 2.3 Hz, 1H), 7.69 (dd, J= 2.4, 8.7 Hz, 1H), 7.52 (d, J= 8.1 Hz, 2H), 7.34 (d, J= 8.3 Hz, 2H), 6.61 (d, J= 4.7 Hz, 1H), 6.57 (s, 1H), 6.52 (d, J= 8.7 Hz, 1H), 3.66 (s, 2H), 2.80 (d, J= 4.9 Hz, 3H), 1.27 (s, 9H). LC- MS (ESI) m/z 365 (M +H)+.

Statistics shows that 84539-30-0 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-N-methylpyridin-2-amine.

Reference:
Patent; AMBIT BIOSCIENCES CORPORATION; ABRAHAM, Sunny; HOLLADAY, Mark, W.; LIU, Gang; XU, Shimin; WO2011/22473; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 84539-30-0, name is 5-Bromo-N-methylpyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows. Formula: C6H7BrN2

a) tert-butyl 5-methoxy-2-[6-(methylamino)pyridin-3-yl]-lH-indole-l-carboxylate l-(tert-Butoxycarbonyl)-5-methoxyindole-2-boronic acid (2 mmol), 5-bromopyridine-2- methylamine (2 mmol), Pd(dppf)Cl2 (0.10 mmol) and 2M Na2CO3 (aq.) (3 mL) were mixed in THF/water 5:1 (10 mL) in a 20 mL microwave vial. The reaction mixture was stirred at 1200C in the microwave reactor for 15 min. Water was added and the solution was extracted with EtOAc. The organic extracts were dried over Na2SO4, filtered and concentrated. The crude mixture was purified by flash chromatography (Heptane/EtOAc gradient) to afford the title intermediate (256 mg). 1H NMR delta ppm 8.04 (d, 1 H) 7.94 (d, 1 H) 7.43 (dd, 1 H) 7.08 (d, 1 H) 6.89 (dd, 1 H) 6.64 (d, 1 H) 6.53 (s, 1 H) 6.50 (d, 1 H) 3.78 (s, 3 H) 2.80 (d, 3 H) 1.36 (s, 9 H); MS m/z (M+H) 354.

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Reference:
Patent; ASTRAZENECA AB; WO2008/108729; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 84539-30-0, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 84539-30-0, name is 5-Bromo-N-methylpyridin-2-amine, molecular formula is C6H7BrN2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

NaHMDS (1 M, 12 mL) was added slowly to a mixture of 5-bromo-2-(N-methylamino)pyridine (2.0 g, 10.7 mmol) and (Boc)2O (2.8 g, 12.8 mmol, 3.0 mL) in THF (20 mL) at 0 C under N2. The resulting mixture was allowed to warm to 20 C and stirred for 13 hours. TLC (petroleum ether / ethyl acetate = 3/1) showed trace amount of compound 64 and a major new spot with lower polarity. The mixture was quenched with sat. NaHCO3 (30 mL) and extracted with EtOAc (50 mL x 2). The organic layers were combined, washed with brine (30 mL), dried over Na2SO4, filtered and concentrated to give a residue. The residue was purified by silica gel column chromatography (petroleum ether / ethyl acetate = 10/1 to 3/1) to give 5-bromo-2-(N-methyl-N-(t-butoxycarbonyl)amino)pyridine (2.8 g, 91% yield) as a light yellow liquid. 1H NMR 400 MHz CDCl3 8.40 – 8.39 (m, 1H), 7.71 – 7.65 (m, 2H), 3.37 (s, 3H), 1.49 (s, 9H). ESI-MS (m/z): 287.0 (M+H)+.

According to the analysis of related databases, 84539-30-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CS PHARMASCIENCES, INC.; SONG, Yuntao; BRDIGES, Alexander, James; (524 pag.)WO2017/120429; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem