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

HRID 606865노트

반응식

HRID 606865 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 2723810Sodium Formate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6df40998fc094812bd0c24e197d446db
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915424B2

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