Methyl iodide → HCID 12136961, compound

HRID 1760226Notes

Reaction equation

HRID 1760226 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:16]([C:17]3[CH:18]=[CH:19][C:20]([OH:23])=[N:21][CH:22]=3)[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:24][O-].[Na+].CI.[Cl-].[NH4+]>C(OCC)(=O)C.O1CCCC1.CO>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:16]([C:17]3[CH:18]=[CH:19][C:20](=[O:23])[N:21]([CH3:24])[CH:22]=3)[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 10942334Sodium MethoxideHCID 178516226HCID 178516226, compound

Product 1

HCID 12136961HCID 12136961, compoundYield 61.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 250 mg of 5-[2-(3-fluorophenyl)-3H-imidazo [4,5-b]pyridin-3-yl]-2-pyridinol, 177 mg of sodium methoxide and 306 μL methyl iodide in a mixture (10 mL) of methanol and tetrahydrofuran in a ratio of 1/1 was stirred at room temperature for 1 day. Ethyl acetate and a saturated aqueous ammonium chloride solution were added thereto and the mixture was extracted 3 times with ethyl acetate. The organic layer was washed once with brine and dried over magnesium sulfate followed by distilling the solvent away under reduced pressure, to give crude crystals. The resulting crude crystals were collected by filtration with diethyl ether, to give 160 mg of the title compound as brown crystals (61% y.).

Workup

  1. extractionthe mixture was extracted 3 times with ethyl acetate
  2. washThe organic layer was washed once with brine
  3. dry with materialdried over magnesium sulfate
  4. distillationby distilling the solvent away under reduced pressure
  5. customto give crude crystals
  6. filtrationThe resulting crude crystals were collected by filtration with diethyl ether

Sources & evidence

ORD record
ord-f8e5b2a902f44f4db44773e8d32e11c7
Source dataset
uspto-grants-2005_01
Patent number
US06841549B1

Reaction notes

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