Electric Literature of 25676-75-9, The chemical industry reduces the impact on the environment during synthesis 25676-75-9, name is 4-Bromo-1-methylimidazole, I believe this compound will play a more active role in future production and life.
Borylation: A flask is charged with Int 39 (458 mg, 1 mmol, 1 eq.), E^pim (381 mg, 1.5 mmol, 1.5 eq.), dioxane previously degassed with N2 (5 mL), potassium acetate (295 mg, 3 mmol, 3 eq.) and Pd(dppf)Cl2-DCM (82 mg, 0.10 mmol, 0.1 eq.). The mixture is stirred to 100 C overnight, concentrated in vacuo. The residue is diluted in DCM and water. The organic layer is separated and concentrated in vacuo, purified by flash chromatography on silica gel (eluting with DCM/MeOH 100/0 to 95/5) to afford the expected boronic ester and boronic acid mixture.LCMS: MW (calcd): 505.3; m/z MW (obsd): 506.3 (M+H).LCMS: MW (calcd): 423.1 ; m/z MW (obsd): 424.1 (M+H).; Suzuki coupling: To a stirred solution of boronic ester and boronic acid mixture (51 mg, 0.10 mmol, 1 eq.) and 4-bromo-l -methyl-imidazole (CAS 25676-75-9; 10 pL, 0.10 mmol, 1 eq.) in dioxane (2 mL) is added CS2CO3 (65 mg, 0.20 mmol, 2 eq.), Pd(PPh3)4 (12 mg, 0.01 mmol, 0.1 eq.) in water (0.5 mL). The mixture is heated to 90 C for 1 h then concentrated in vacuo. The residue is diluted in DCM and water. The organic layer is separated and concentrated in vacuo, purified by flash chromatography on Biotage SNAP KP-NH cartridge (eluting with DCM/MeOH 100/0 to 98/2) to afford the expected compound.
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 4-Bromo-1-methylimidazole, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; GALAPAGOS NV; ALVEY, Luke, Jonathan; ANNOOT, Denis, Maurice; BONNATERRE, Florence, Marie-Emilie; BUCHER, Denis; DUTHION, Beranger; JARY, Helene; PEIXOTO, Christophe; TEMAL-LAIB, Taoues; TIRERA, Amynata; (340 pag.)WO2019/105886; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem