Methyl iodide → 5-(4-Fluoro-3-methoxyphenylethynyl)-nicotinonitrile

HRID 606865Notes

Reaction equation

HRID 606865 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:9]#[C:10][C:11]2[CH:12]=[N:13][CH:14]=[C:15]([CH:18]=2)[C:16]#[N:17])[CH:5]=[CH:6][C:7]=1[F:8].IC.[C:21](=O)([O-])[O-].[K+].[K+]>C(#N)C.C([O-])=O.[Na+]>[F:8][C:7]1[CH:6]=[CH:5][C:4]([C:9]#[C:10][C:11]2[CH:12]=[N:13][CH:14]=[C:15]([CH:18]=2)[C:16]#[N:17])=[CH:3][C:2]=1[O:1][CH3:21]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 670478145-(3-Hydroxy-4-fluorophenylethynyl)-nicotinonitrile

Product 1

HCID 670476015-(4-Fluoro-3-methoxyphenylethynyl)-nicotinonitrileYield 44%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 2723810Sodium FormateSolvent

Procedure

Dissolve 5-(3-hydroxy-4-fluorophenylethynyl)-nicotinonitrile, (prepared essentially as described in EXAMPLE 77), (150 mg, 0.63 mmol) in anhydrous acetonitrile (5 mL) and sequentially add iodomethane (59 μL, 0.95 mmol) and potassium carbonate (174 mg, 1.26 mmol). Stir at room temperature for 12 h, dilute with an aqueous saturated solution of sodium carbanate and extract with dichloromethane. Sequentially wash the organic layer with water and an aqueous saturated solution of sodium chloride, dry (magnesium sulfate), filter and concentrate. Purify by silica gel chromatography, eluting with 30:70 ethyl acetate:hexanes, to give the title compound (70 mg, 44%) as white solid.

Workup

  1. custom(prepared essentially
  2. extractionextract with dichloromethane
  3. washSequentially wash the organic layer with water
  4. dry with materialan aqueous saturated solution of sodium chloride, dry (magnesium sulfate)
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify by silica gel chromatography
  8. washeluting with 30:70 ethyl acetate

Sources & evidence

ORD record
ord-6df40998fc094812bd0c24e197d446db
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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