Diethyl Ether → HCID 86716068, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-bromo-1-methyl-1H-imidazole (0.964 g, 5.99 mmol) in CH2Cl2 (6 mL) at room temperature was added 3.0 Methylmagnesium bromide in Et2O (2.0 mL, 6.00 mmol) dropwise. The mixture changed to a white suspension briefly then to clear yellow. After 15 min stirring, the mixture was cooled to 4° C. A solution of 2-fluoro-N-methoxy-N-methylisonicotinamide (1.05 g, 5.70 mmol, Intermediate 13, step a) in CH2Cl2 (6 mL) was introduced via cannula and some hard solid formed. The cooling bath was removed, and the mixture was stirred for 2 days. NH4Cl (aqueous) was added, the organic layer was separated, and the aqueous layer was extracted with EtOAc. The combined organic layers were dried (Na2SO4), filtered, and concentrated. The residue was diluted with small amount of CH2Cl2. The undissolved solid was filtered, washed with Et2O, and dried under vacuum to provide the title compound as a white solid. The filtrate was concentrated and purified by flash column chromatography (40 g silica gel column, 100% EtOAc) to give more title compound.

Provenance & Evidence