Methyl p-toluenesulfonate → HCID 57653371, compound

Temperature

2.5 °C

To crude 4-methoxy-2-(1H-imidazol-2-yl)pyridine (0.40 g, 2.28 mmol) in 7.5 mL anhydrous DMF with magnetic stirring under Ar at 0° C., NaH (60% in oil, 91 mg, 2.28 mmol) was added portionwise. Stirred at 0-5° C. for 1 h, then added a solution of methyl-p-toluenesulfonate (0.344 mL, 2.28 mmol) in 0.75 mL anh. DMF dropwise with stirring. After 15 min, the ice bath was removed and the reaction mixture stirred for 2 h at room temp. Cooled back to 0° C. and quenched by very carefully adding 10% aq. Na2CO3 dropwise (about 10 mL total). Extracted 2×30 mL chloroform. Combined organic layers were washed with brine (5 mL), dried over Na2SO4 and concentrated to give 0.73 g as a dual-phase oil. Chromatographed on 18 g silica gel in 0-2% MeOH/CHCl3+0.5% TEA to yield 0.20 g (45%) of 4-methoxy-2-(1-methyl-1H-imidazol-2-yl)pyridine.

1. stirringwith stirring
2. waitAfter 15 min
3. customthe ice bath was removed
4. stirringthe reaction mixture stirred for 2 h at room temp
5. temperatureCooled back to 0° C.
6. customquenched
7. additionby very carefully adding 10% aq. Na2CO3 dropwise (about 10 mL total)
8. extractionExtracted 2×30 mL chloroform
9. washCombined organic layers were washed with brine (5 mL)
10. dry with materialdried over Na2SO4
11. concentrationconcentrated
12. customto give 0.73 g as a dual-phase oil
13. customChromatographed on 18 g silica gel in 0-2% MeOH/CHCl3+0.5% TEA

ORD record

ord-2835c354da8842d7a82ebdfcdd230f9b

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08262874B2