Potassium Carbonate → 1-(3-Fluoro-4-methylpyridin-2-yl)-1H-imidazole-4-carboxylic acid

HRID 1508340Notes

Reaction equation

HRID 1508340 reaction equation
[F:1][C:2]1[C:3]([N:9]2[CH:13]=[C:12]([C:14]([O:16]C)=[O:15])[N:11]=[CH:10]2)=[N:4][CH:5]=[CH:6][C:7]=1[CH3:8].N1C=C(C(OC)=O)N=C1.BrC1C(F)=C(C)C=CN=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.[Cu]I>[F:1][C:2]1[C:3]([N:9]2[CH:13]=[C:12]([C:14]([OH:16])=[O:15])[N:11]=[CH:10]2)=[N:4][CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 404251182-Bromo-3-fluoro-4-methylpyridineHCID 71255701Methyl 1-(3-fluoro-4-methylpyridin-2-yl)-1H-imidazole-4-carboxylateHCID 178418785HCID 178418785, compound

Product 1

HCID 712554391-(3-Fluoro-4-methylpyridin-2-yl)-1H-imidazole-4-carboxylic acidYield 3%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

Methyl 1-(3-fluoro-4-methylpyridin-2-yl)-1H-imidazole-4-carboxylate: A suspension of methyl 1H-imidazole-4-carboxylate (83 mg, 0.658 mmol), 2-bromo-3-fluoro-4-methylpyridine (200 mg, 1.053 mmol), copper (I) iodide (125 mg, 0.658 mmol) and potassium carbonate (546 mg, 3.95 mmol) in DMSO (2 mL) was heated at 120° for 90 min under microwave conditions. The reaction mixture was quenched with H2O, and the solid was suspended in EtOAc and MeOH. The combined organic layer was concentrated in vacuo, yielding oily residue, which was purified by reverse phase HPLC to give the desired product (5 mg, 3%). MS(ESI) m/z: 236.1 (M+H)+.

Workup

  1. temperaturewas heated at 120° for 90 min under microwave conditions
  2. customThe reaction mixture was quenched with H2O
  3. concentrationThe combined organic layer was concentrated in vacuo
  4. customyielding oily residue, which
  5. customwas purified by reverse phase HPLC

Sources & evidence

ORD record
ord-c158f72bfb454ef2af89f937d853ee1e
Source dataset
uspto-grants-2015_12
Patent number
US09221818B2

Reaction notes

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