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

HRID 1487876Notes

Reaction equation

HRID 1487876 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:14]=1[CH3:15])[C:8]([O:10][CH3:11])=[O:9])=O.Cl.[CH3:17][O:18][CH2:19][C:20](=[NH:22])[NH2:21].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:17][O:18][CH2:19][C:20]1[NH:21][C:3]([C:5]2[CH:6]=[C:7]([CH:12]=[CH:13][C:14]=2[CH3:15])[C:8]([O:10][CH3:11])=[O:9])=[CH:2][N:22]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 135486022-Methoxyethanimidamide hydrochloride2×HCID 90021973Methyl 3-(2-bromoacetyl)-4-methylbenzoate2×

Product 1

HCID 90030068Methyl 3-(2-(methoxymethyl)-1H-imidazol-5-yl)-4-methylbenzoateYield 19%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-14b7b6415dcf4ad6b0f1d054e73ae2ac
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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