Category: 219814-29-6

These common heterocyclic compound, 219814-29-6, name is 2,5-Dibromo-4-methylimidazole, 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. Recommanded Product: 2,5-Dibromo-4-methylimidazole

[Example 6]; While a mixture of 23.9 g (100.0 mmol) of 2,4-dibromo-5-methylimidazole, 29.4 g (300.0 mmol) of cyclohexanone, and 23.9 g (259.4 mmol) of toluene was stirred at ordinary temperature, 22.5 g (150.0 mmol) of sodium iodide was added thereto to prepare a reaction liquid. After the reaction liquid was stirred at 105C for 12 hours under a nitrogen stream, the liquid was stirred under ice cooling for 1 hour. When 2-bromo-4-methylimidazole in the reaction liquid was analyzed by means of HPLC, it was confirmed that the product was formed in an amount of 13.7 g (82.3 mmol, conversion: 85.3%). After the reaction liquid was concentrated under reduced pressure, the product was purified by silica gel chromatography (ethyl acetate/hexane system) and, after volatile matter was further vaporized to solidify the product, crystals of 2-bromo-4-methylimidazole were obtained in an amount of 12.6 g (yield: 78.1%) as a residue. Incidentally, the NMR spectrum of the crystals was measured and was compared with the NMR spectrum of its specimen, whereby it was confirmed that the product is 2-bromo-4-methylimidazole.

The synthetic route of 2,5-Dibromo-4-methylimidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SHIKOKU CHEMICALS CORPORATION; EP2141151; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 219814-29-6, name is 2,5-Dibromo-4-methylimidazole, molecular formula is C4H4Br2N2, 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. Computed Properties of C4H4Br2N2

[0304] To a solution of 18-1 (3.6 g, 15 mmol) and K2C03 (4.1 g, 30 mmol) in DMF ( 18 mL) was added iodomethane ( 1 .4 mL, 23 mmol) at 25C. The solution was stirred for 1 5 h. The mixture was poured into water and extracted with EA The combined organic phase was dried over anhydrous Na?S04, and the residue was purified by chromatography on silica gel (EA/hexane) to giv e 18-2 (1 .6 g, 41 %). NMR (400 MHz, CDC13): delta 3.52 (s. 3H). 2.21 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 219814-29-6, its application will become more common.

Reference:
Patent; ALIOS BIOPHARMA, INC.; WANG, Guangyi; BEIGELMAN, Leonid; TRUONG, Anh; NAPOLITANO, Carmela; ANDREOTTI, Daniele; HE, Haiying; STEIN, Karin, Ann; WO2015/26792; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 219814-29-6,Some common heterocyclic compound, 219814-29-6, name is 2,5-Dibromo-4-methylimidazole, molecular formula is C4H4Br2N2, 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.

Step A : (5-Bromo-6-methyl-3 H- 1 ‘ -azaspiro [imidazo [2, 1 -b] oxazole-2,3 ‘ – bicyclo[2.2.2]octan]-l ‘-yl-8-ium)trihydroborate and (6-bromo-5-methyl-3H-l ‘- azaspiro[imidazo[2, l-b]oxazole-2,3 ‘-bicyclo[2.2.2]octan]- -yl-8-ium)trihydroborate To 2,4-dibromo-5-methyl-lH-imidazole (0.8 g, 3.3 mmol) in THF (25 niL) was added N-butyllithium (1.3 niL, 3.3 mmol) dropwise at -78C. After 45 minutes, a solution of racemic r-azaspiro[oxirane-2,3′-bicyclo[2.2.2]octan]-l’-yl-4- ium)trihydroborate (0.56 g, 3.7 mmol) from the reference example, in THF (20 mL) was added dropwise at -78C. The cooling bath was removed and the reaction mixture warmed to room temperature. After 15 minutes, the mixture was heated to 75C for 2 hours and then cooled to room temperature. The reaction was quenched with water and the product was extracted with ethyl acetate (100 mL). The organics were dried with MgS04, filtered and the solvent was removed to yield the crude product. The crude material was purified by chromatography (Biotage) to yield the regioisomeric products. These regioisomers were separated by reverse phase chromatography using a Sunfire column with gradients of acetonitrile-water containing 0.1% of trifluoroacetic acid (TFA), and at 40 mL/min flow rate. The pure fractions for peak 1 and peak 2 were then neutralized with 1 N NaOH (pH ~8-9) and the products were extracted with ethyl acetate. The organic layers were dried with MgS04, filtered and the solvent was removed to yield racemic (5-bromo-6-methyl-3H-l’-azaspiro[imidazo[2,l-b]oxazole-2,3′- bicyclo[2.2.2]octan]-l’-yl-8-ium)trihydroborate (0.32 g, 1.0 mmol, 30.8 % yield) XH NMR (500MHz, DMSO-d6) delta 4.23 (d, J=9.8 Hz, IH), 4.12 (d, J=9.9 Hz, IH), 3.36 (dd, J=15.2, 2.5 Hz, IH), 3.19 (dd, J=15.3, 2.1 Hz, IH), 3.04 – 2.95 (m, IH), 2.91 – 2.73 (m, 3H), 2.35 (br. s., IH), 2.03 – 1.88 (m, 4H), 1.84 – 1.67 (m, 3H), 1.64 – 1.11 (m, 3H). MS (LC/MS) R.T. = 2.09; [M+2]+ = 300.04 and racemic (6-bromo-5-methyl-3H-l’- azaspiro[imidazo[2,l-b]oxazole-2,3′-bicyclo[2.2.2]octan]-r-yl-8-ium)trihydroborate (0.33 g, 1.1 mmol, 31.7 % yield) as powders. NMR (500MHz, DMSO-de) delta 4.32 (d, J=10.1 Hz, IH), 4.12 (d, J=10.2 Hz, IH), 3.36 (d, J=2.4 Hz, IH), 3.18 (dd, J=15.2, 2.2 Hz, IH), 2.99 (d, J=2.9 Hz, IH), 2.93 – 2.78 (m, 3H), 2.31 (d, J=2.0 Hz, IH), 2.06 – 1.94 (m, 4H), 1.84 – 1.69 (m, 3H), 1.62 – 1.22 (m, 3H). MS (LC/MS) R.T. = 2.64; [M+2]+ = 300.04.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,5-Dibromo-4-methylimidazole, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; COOK II, James H.; ZUSI, F. Christopher; HILL, Matthew D.; (87 pag.)WO2016/73407; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 219814-29-6, These common heterocyclic compound, 219814-29-6, name is 2,5-Dibromo-4-methylimidazole, 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.

[Example 6]; While a mixture of 23.9 g (100.0 mmol) of 2,4-dibromo-5-methylimidazole, 29.4 g (300.0 mmol) of cyclohexanone, and 23.9 g (259.4 mmol) of toluene was stirred at ordinary temperature, 22.5 g (150.0 mmol) of sodium iodide was added thereto to prepare a reaction liquid. After the reaction liquid was stirred at 105C for 12 hours under a nitrogen stream, the liquid was stirred under ice cooling for 1 hour. When 2-bromo-4-methylimidazole in the reaction liquid was analyzed by means of HPLC, it was confirmed that the product was formed in an amount of 13.7 g (82.3 mmol, conversion: 85.3%). After the reaction liquid was concentrated under reduced pressure, the product was purified by silica gel chromatography (ethyl acetate/hexane system) and, after volatile matter was further vaporized to solidify the product, crystals of 2-bromo-4-methylimidazole were obtained in an amount of 12.6 g (yield: 78.1%) as a residue. Incidentally, the NMR spectrum of the crystals was measured and was compared with the NMR spectrum of its specimen, whereby it was confirmed that the product is 2-bromo-4-methylimidazole.

Statistics shows that 2,5-Dibromo-4-methylimidazole is playing an increasingly important role. we look forward to future research findings about 219814-29-6.

Reference:
Patent; SHIKOKU CHEMICALS CORPORATION; EP2141151; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 219814-29-6, name is 2,5-Dibromo-4-methylimidazole, 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. Quality Control of 2,5-Dibromo-4-methylimidazole

[Example 6]; While a mixture of 23.9 g (100.0 mmol) of 2,4-dibromo-5-methylimidazole, 29.4 g (300.0 mmol) of cyclohexanone, and 23.9 g (259.4 mmol) of toluene was stirred at ordinary temperature, 22.5 g (150.0 mmol) of sodium iodide was added thereto to prepare a reaction liquid. After the reaction liquid was stirred at 105C for 12 hours under a nitrogen stream, the liquid was stirred under ice cooling for 1 hour. When 2-bromo-4-methylimidazole in the reaction liquid was analyzed by means of HPLC, it was confirmed that the product was formed in an amount of 13.7 g (82.3 mmol, conversion: 85.3%). After the reaction liquid was concentrated under reduced pressure, the product was purified by silica gel chromatography (ethyl acetate/hexane system) and, after volatile matter was further vaporized to solidify the product, crystals of 2-bromo-4-methylimidazole were obtained in an amount of 12.6 g (yield: 78.1%) as a residue. Incidentally, the NMR spectrum of the crystals was measured and was compared with the NMR spectrum of its specimen, whereby it was confirmed that the product is 2-bromo-4-methylimidazole.

The synthetic route of 2,5-Dibromo-4-methylimidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SHIKOKU CHEMICALS CORPORATION; EP2141151; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem