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

HRID 606865ノート

反応式

HRID 606865 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

HCID 670476015-(4-Fluoro-3-methoxyphenylethynyl)-nicotinonitrile収率 44%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 2723810Sodium Formate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6df40998fc094812bd0c24e197d446db
出典データセット
uspto-grants-2011_03
特許番号
US07915424B2

反応ノート

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