Methyl iodide → HCID 68008682, compound

HRID 533157Notes

Reaction equation

HRID 533157 reaction equation
IC.[Cl:3][C:4]1[C:5]([C:18]([OH:20])=[O:19])=[N:6][CH:7]=[C:8]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:9]=1.[C:21]([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:21][O:19][C:18]([C:5]1[C:4]([Cl:3])=[CH:9][C:8]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:7][N:6]=1)=[O:20]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 68008777HCID 68008777, compound

Product 1

HCID 68008682HCID 68008682, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Iodomethane (0.4 mL, 6.39 mmol) was added to a suspension of 3-chloro-5-phenoxymethyl-pyridine-2-carboxylic acid (265 mg, 1.92 mmol) and K2CO3 (265 mg, 1.92 mmol) in DMF (15 mL) in a sealed tube. The mixture was stirred at RT for 16 h. The solvent was evaporated in vacuo and the mixture was diluted with H2O and extracted with EtOAc. The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica; EtOAc in DCM 0/100 to 70/30). The desired fractions were collected and the solvents evaporated in vacuo to yield 3-chloro-5-phenoxymethyl-pyridine-2-carboxylic acid methyl ester (258 mg, 73%) as a colorless oil.

Workup

  1. customThe solvent was evaporated in vacuo
  2. additionthe mixture was diluted with H2O
  3. extractionextracted with EtOAc
  4. customThe organic layer was separated
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvents evaporated in vacuo
  8. customThe crude product was purified by flash column chromatography (silica; EtOAc in DCM 0/100 to 70/30)
  9. customThe desired fractions were collected
  10. customthe solvents evaporated in vacuo

Sources & evidence

ORD record
ord-36283885000345ee82b2ec8d381ced06
Source dataset
uspto-grants-2014_10
Patent number
US08853237B2

Reaction notes

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