Some common heterocyclic compound, 1848-84-6, name is 2-Ethyl-1H-benzo[d]imidazole, molecular formula is C9H10N2, 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. Application In Synthesis of 2-Ethyl-1H-benzo[d]imidazole
A mixture of 3-(2-chloro-9-methyl-6-morpholin-4-yl-9H-purin-8-yl)- pyrrolidine-1-carboxylic acid tert-butyl ester (44 mg, 0.10 mmol), 2-ethylbenzimidazole (17 mg, 0.11 mmol), Pd2(dba)3 (2.4 mg, 2.5 molpercent), Xphos (5.0 mg, 10 molpercent) and Cs2CO3 (51 mg, 0.16 mmol) in dioxane (1.5 mL) was purged with argon gas then heated at 120 °C, for 20 h, in a sealed tube. The reaction mixture was loaded onto an Isolute.(R). SCX-2 cartridge, washed with MeOH then the desired product eluted with 2 M NH3/Me0H in DCM. The resulting residue was purified by column chromatography (Si-PCC, 0-100percent EtOAc in cyclohexane) to give 646 (37 mg, 67percent) as a yellow solid. LCMS: (Method I): RT 4.34 min, [M+H]+ 533.2 1H NMR (400 MHz, CDCl3d): delta 8.01-7.97 (m, 1 H), 7.78-7.73 (m, 1 H), 7.29- 7.22 (m, 2 H), 4.55-4.10 (m, 4 H), 3.86 (t, J = 4.67 Hz, 4 H), 3.80 (s, 3 H), 3.80-3.44 (m, 4 H), 3.35 (q, J = 7.48 Hz, 2 H), 2.36 (s, 3 H), 1.49 (s, 9 H), 1.44 (t, J = 7.48 Hz, 3 H)
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1848-84-6, its application will become more common.
Reference:
Patent; GENENTECH, INC.; F. HOFFMANN-LA ROCHE AG; CASTANEDO, Georgette; CHAN, Bryan; GOLDSTEIN, David Michael; KONDRU, Rama K.; LUCAS, Matthew C.; PALMER, Wylie Solang; PRICE, Stephen; SAFINA, Brian; SAVY, Pascal Pierre Alexandre; SEWARD, Eileen Mary; SUTHERLIN, Daniel P.; SWEENEY, Zachary Kevin; WO2010/138589; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem