Methyl iodide → HCID 86674105, compound

HRID 1888336Notes

Reaction equation

HRID 1888336 reaction equation
CI.[S:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[C:8]1[NH:9][CH:10]=[C:11]([CH:13]=[O:14])[N:12]=1.[C:15](=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:15][N:12]1[C:11]([CH:13]=[O:14])=[CH:10][N:9]=[C:8]1[C:4]1[S:3][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178519862HCID 178519862, compound

Product 1

HCID 86674105HCID 86674105, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
70 °C

Procedure

Methyl iodide (477 mg, 3.36 mmol) dissolved in DMF (0.5 ml) was added dropwise to a stirred solution of 2-Thiophen-2-yl-1H-imidazole-4-carbaldehyde (0.57 g, 3.2 mmol) and Potassium carbonate (0.486 g, 3.52 mmol) in dry N,N-Dimethylformamide (6 mL) at rt. The solution was stirred at 70° C. 3 h. Most of the DMF was evaporated off and the residue was partioned between EtOAc (50 ml) and brine (25 ml). The phases were separated and the organic phase was dried (Na2SO4) and the solvent was evaporated off. The crude product was purified by silica gel chromatography (Eluent: 50%-100% EtOAc in n-heptane). Yield: 211 mg of the title compound as an oil. H-NMR (DMSO-d6): δ 9.71 (s, 1H), 7.80 (s, 1H) 7.54 (m, 2H), 7.17 (m, 1H), 4.14 (s, 3H). LC-MS: m/z=192.9 (MH+), tR=0.34 min, method C. (211 mg of a fast eluting isomer (3-Methyl-2-thiophen-2-yl-3H-imidazole-4-carbaldehyde) was also isolated and discarded).

Workup

  1. custom3 h
  2. customMost of the DMF was evaporated off
  3. customThe phases were separated
  4. dry with materialthe organic phase was dried (Na2SO4)
  5. customthe solvent was evaporated off
  6. customThe crude product was purified by silica gel chromatography (Eluent: 50%-100% EtOAc in n-heptane)

Sources & evidence

ORD record
ord-ed53d80a838c4411950023e53b945042
Source dataset
uspto-grants-2013_08
Patent number
US08501797B2

Reaction notes

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