Category: 25676-75-9

Some common heterocyclic compound, 25676-75-9, name is 4-Bromo-1-methylimidazole, molecular formula is C4H5BrN2, 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. category: imidazoles-derivatives

To a solution of compound 82-1 (0.04 g, 0.10 mmol, 1.0 eq) and compound 82-2 (1104) (16.3 mg, 0.10 mmol, 1.0 eq) in dioxane (5.0 mL) was added H20 (0.5 mL) Pd(dppf)Cl2 (7.4 mg, 10.14 umol, 0.1 eq) and Na2C03 (21.5 mg, 0.20 mmol, 2.0 eq). The mixture was stirred at 80 C for 16 hour under N2 atmosphere. LCMS showed desired compound was found. The reaction was filtered through Celite and concentrated under reduced pressure to give a residue. The crude product was purified by prep-HPLC to give Compound 82 (6.64 mg, 18.86 umol, 18.60% yield). LCMS (ESI): RT = 0.634 min, mass calc. for Ci7H24N402S 348.16, m/z found 348.9 [M+H]+; 1HNMR (400 MHz, CDC13) delta 8.55 (s, 1H), 7.81 (d, J = 2.0 Hz, 1H), 7.54 (dd, J = 2.3, 8.8 Hz, 1H), 7.47 (s, 1H), 7.24 (s, 1H), 6.69 (d, J = 9.0 Hz, 1H), 4.24 (q, J= 5.4 Hz, 1H), 3.75 (s, 3H), 3.44 (s, 1H), 2.62 (d, J = 5.5 Hz, 3H), 2.12 – 2.00 (m, 2H), 1.86 – 1.75 (m, 2H), 1.69 – 1.64 (m, 1H), 1.48 – 1.25 (m, 5H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 25676-75-9, its application will become more common.

Reference:
Patent; VIVACE THERAPEUTICS, INC.; KONRADI, Andrei W.; LIN, Tracy Tzu-Ling Tang; (294 pag.)WO2019/40380; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 25676-75-9,Some common heterocyclic compound, 25676-75-9, name is 4-Bromo-1-methylimidazole, molecular formula is C4H5BrN2, 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.

[00288] A mixture of5-(4-methylpiperazin-1-ylmethyl)-furan-2-carboxylic acid [8- (4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl]-amide (98 mg, 0.18 mmol, 1.0 eq), 4-bromo-1 -methyl-1H-imidazole (63 mg, 0.39 mmol, 2.2 eq.) Pd(PPh3)4 (21 mg, 0.017 mmol, 0.1eq), K2CO3 (49 mg, 2.0 eq) in 9:1 dioxane:H20 (5ml_) was purged with N2 for 15 min and the mixture was heated to 110 C for 1 h. The reaction mixture was concentrated under reduced pressure and the residue dissolved in MeOH and loaded onto a SCX-2 cartridge. The cartridge was washed with MeOH, and the compound eluted using 0.5M ammonia in methanol. The product-containing fractions were concentrated under reduced pressure to yield the crude material which was purified by prep HPLC to give 5-(4- methyl-piperazin-1-ylmethyl)-furan-2-carboxylic acid [8-(1 -methyl-1H-imidazol-4-yl)-2,3- dihydro-benzo[1,4]dioxin-2-ylmethyl]-amide (13.3 mg, 16.4 %) as an off-white solid AnalpH9_MeOH_QC_V1 : Rt: 6.93 min, m/z 452.4 [M+H]+ 1H NMR (400MHz, DMSO-d6): d 8.65 (t, J = 6.0Hz, 1H) 7.62-7.57 (m, 3H) 7.13 (d, J = 3.5 Hz, 1H) 6.82 (t, J = 7.3 Hz, 1H) 6.70 (dd, J = 7.8, 1.5 Hz, 1H) 6.46 (d, J = 3.3 Hz, 1H) 4.42-4.35 (m, 2H) 3.97 (dd, J = 1 1.9, 8.6 Hz, 2H) 3.77-3.68 (m, 1H) 3.56 (s, 3H) 3.51 (s, 2H) 2.48-2.20 (m, 8H) 2.16 (s, 3H)

The synthetic route of 25676-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; OXFORD UNIVERSITY INNOVATION LIMITED; RABBITTS, Terrence; QUEVEDO, Camilo; CRUZ, Abimael; PHILIPS, Simon; FALLON, Philip Spencer; DUNN, Jonathan Neil; FREEM, Joshua Robert; LEE, Lydia Yuen-Wah; TRAORE, Tenin; WILLIAMS, Sophie Caroline; (219 pag.)WO2019/145718; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem