Related Products of 4887-88-1, These common heterocyclic compound, 4887-88-1, name is 5-Bromo-1H-benzo[d]imidazole, 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.
Step C – Methyl 5-{5-bromo-1 A£benztmidazoi-1-yl)-3-{[f°/£ butyl{dimethyi)si.yl]oxy}thlophene-2-carboxyiate and methyl 5-(6-bromo1 H- be?zimldazo.-1-yl)-3″{[/erf”btyf(dimethyi)silyl]oxy}thiophene-2-carboxy.ate {title compounds)To a solution of crude, impure 5-bromobe?zimidazo.e (48.2 g) and methyl 2- chioro-3-oxo-2,3-dihydrothiophene-2-carboxylate (42 g, 220 mmol) In 800 mL of CHCl3 was added Mmethyiimidazote (28 rrsL, 350 mmol). After 16 h, N- roethyl imidazole (17 mL, 220 mmol) and (38 g, 240 mmoi) was added. When TLC showed the reaction to be complete, the solution was diluted with water. The layers were separated. The organic phase was washed with water, dried over MgSO4 and concentrated onto ceiite. The crude mixture was purified by flash column chromatography (Q- 25% EtOAc:hexa?es) in batches to separate the 2 regioisomers, giving 33.5 g of Intermediate 4 eluiing first and 29.2 g of Intermediate 5 elupsilonti?g second (58%), (Intermediate 4, 5~thetar) 1H NMR (400 MHz, drthetayUSDG) delta 8.77 (s, 1H)1 8.01 (d J – 1.6 Hz, IH), 7.76 (d, J -8.8 Hz1 IH)1 7.56{dd, J ^8.8 and 1.6 Hz5 1 H)1 7.25 (s, 1 H), 3.76 (s, 3H)1 0.99 {s, 9H), 0.27 (ss 6H). (trfermediate 5, 6- Br) 1H NyR (400 MHz1 (J6-DMSO) delta 8.71 (S1 1H), 7.88 (d, ./ – 1 ,6 Hz, 1H), 7,73 (d, J ^ 8.8 Hz5 I H), 7.50 (, ./=8.8 and 2.0 Hz1 I H)1 7.28 (s, 1H)1 3.77 (s, 3H), 0.99 (s, 9H), 0.26 (s, 6H).
Statistics shows that 5-Bromo-1H-benzo[d]imidazole is playing an increasingly important role. we look forward to future research findings about 4887-88-1.
Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2007/143456; (2007); A2;,
Imidazole – Wikipedia,
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