Ethyl Acetate → HCID 117803009, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 160h (500 mg, 1.4 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (212 mg, 1.4 mmol) in dimethyl carbonate (100 mL) was stirred at 140° C. for 3 h. See FIG. 5. TLC (petroleum ether:ethyl acetate=3:1) showed that the starting material was completely consumed. The mixture was diluted with water (100 mL) and extracted with EtOAc (100 mL×2). The combined organic layers were washed with brine (60 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (eluting with petroleum ether:ethyl acetate=3:1) to afford (2-(6-(tert-butyl)-1-methyl-1H-benzo[d]imidazol-2-yl)-4-chloropyridin-3-yl)methyl acetate 160i and (2-(5-(tert-butyl)-1-methyl-1H-benzo[d]imidazol-2-yl)-4-chloropyridin-3-yl)methyl acetate 160j as a mixture of regioisomers (480 mg, 92%). MS-ESI: [M+H]+ 372.1.

Provenance & Evidence