Diethyl Ether → 1-[3-(6-chloro-1-methyl-1H-benzoimidazol-2-yl)-pyridin-4-yl]-ethanol

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-(6-chloro-1-methyl-1H-benzoimidazol-2-yl)-pyridine-4-carbaldehyde (75 mg, 0.276 mmol) in THF (4 mL) at −78° C. was added 3 M MeMgBr in diethyl ether (0.138 mL, 0.414 mmol) and the mixture was stirred at −78° C. for 0.5 hr. The reaction was quenched with water (0.5 mL) and the mixture was warmed to room temperature. It was concentrated in vacuo. The crude was taken up in MeOH (5 mL) and purified on RP-HPLC using RP18 column and gradient 0.1% aqueous NH4OH in acetonitrile, followed with a second purification by silica gel flash chromatography DCM-MeOH (9:1) to afford 1-[3-(6-chloro-1-methyl-1H-benzoimidazol-2-yl)-pyridin-4-yl]-ethanol. 1H NMR (400 MHz, MeOD) δ ppm 1.34 (d, J=6.6 Hz, 3H), 3.73 (s, 3H), 4.81-4.86 (m, 1H), 7.38 (dd, J=8.6, 2.0 Hz, 1H), 7.72 (d, J=9.1 Hz, 1H), 7.73 (d, J=2.0 Hz, 1H), 7.86 (d, J=5.3 Hz, 1H), 8.63 (s, 1H), 8.79 (d, J=5.3 Hz, 1H); HRMS: (ESI) ink 288.0894 [(M+H)+ Calcd for C15H14ClN3O 288.0904].

Provenance & Evidence