Benzaldehyde, 4-(4-methyl-1H-imidazol-1-yl)- synthesis

Yield:127404-21-1 700 mg

Reaction Conditions:

with N-ethyl-N,N-diisopropylamine in acetonitrile; for 72 h;Reflux;Inert atmosphere;

Steps:

Intermediate 17

A mixture of 4-fluorobenzaldehyde (1.76 g, 14.18 mmol) and 4-methylimidazole (2.91 g, 35.45 mmol) in acetonitrile (80 mL) was charged with DIEA (6.18 mL, 35.45 mmol). The solution was refluxed for 72 hrs., upon which TLC indicated still 30% starting material was left. The mixture was concentrated on rotavapor to dryness and the resulting crude product was purified by Teledyne-Isco flash system by using 0 to 8% of methanol in dichloromethane to provide intermediate 17 as a viscous solid (700 mg).¹H NMR (400 MHz, DMSO-d₆) δ (ppm): 10.62 (s, 0.48H), 8.96 (s, 0.45 H), 8.63 (m, 2H), 8.46 (m, 2H), 8.09 (s, 1H), 7.30 (s, 1H), 2.79+2.74 (s, 3H). MS (ESI): Calcd for C11H10N2O: 186, found: 187(M+H)⁺.

References:

WO2016/205460,2016,A1 Location in patent:Paragraph 0166-0167