Potassium Carbonate → Methyl 3-(2-(methoxymethyl)-1H-imidazol-5-yl)-4-methylbenzoate

Temperatur

80 °C

Into a 50-mL round-bottom flask, which was purged and maintained with an inert atmosphere of nitrogen, was placed a solution of methyl 3-(2-bromoacetyl)-4-methylbenzoate (compound 27.2, 281 mg, 1.04 mmol) in ACN (5 mL). 2-Methoxyacetimidamide (compound 4.7, 194 mg, 1.56 mmol) and potassium carbonate (434 mg, 3.14 mmol) were added and the resulting mixture was stirred for 12 hours at 80° C., then concentrated under reduced pressure. The residue was diluted with water (50 mL) and extracted with ethyl acetate (3×30 mL). The combined organic layers were washed with brine (3×50 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography with ethyl acetate/petroleum ether (1:1) as the eluent to yield 50 mg (19%) of the title compound as a brown solid.

1. customInto a 50-mL round-bottom flask, which was purged
2. temperaturemaintained with an inert atmosphere of nitrogen
3. concentrationconcentrated under reduced pressure
4. additionThe residue was diluted with water (50 mL)
5. extractionextracted with ethyl acetate (3×30 mL)
6. washThe combined organic layers were washed with brine (3×50 mL)
7. dry with materialdried (Na2SO4)
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure
10. customThe residue was purified by silica gel column chromatography with ethyl acetate/petroleum ether (1:1) as the eluent

ORD-Eintrag

ord-14b7b6415dcf4ad6b0f1d054e73ae2ac

Quelldatensatz

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09428502B2