Methyl iodide → Methyl 2-(4-(3-chloropyrazin-2-yl)phenyl)acetate

HRID 474143

Reaktionsgleichung

Reaktionsgleichung von HRID 474143
[Cl:1][C:2]1[C:3]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C:15]([OH:17])=[O:16])=[CH:10][CH:9]=2)=[N:4][CH:5]=[CH:6][N:7]=1.[C:18](=O)([O-])[O-].[K+].[K+].IC>CN(C=O)C.C(Cl)Cl>[Cl:1][C:2]1[C:3]([C:8]2[CH:9]=[CH:10][C:11]([CH2:14][C:15]([O:17][CH3:18])=[O:16])=[CH:12][CH:13]=2)=[N:4][CH:5]=[CH:6][N:7]=1

Komponenten

6

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 59535937[4-(3-Chloropyrazin-2-yl)phenyl]acetic acid

Produkt 1

HCID 59535943Methyl 2-(4-(3-chloropyrazin-2-yl)phenyl)acetateAusbeute 36 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 0.40 g (1.6 mmol) of [4-(3-chloropyrazin-2-yl)phenyl]acetic acid in 3.0 mL of DMF was added 0.67 g (4.8 mmol) of potassium carbonate and 0.14 mL (2.3 mmol) iodomethane. After 1 h at 40° C., the reaction mixture was cooled, diluted with CH2Cl2, washed three times with water followed by brine. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. Purification by flash chromatography (silica gel, linear gradient 0-75% EtOAc in hexanes) afforded 0.15 g (36%) methyl [4-(3-chloropyrazin-2-yl)phenyl]acetate. ES-MS M+1=263.0.

Aufarbeitung

  1. temperaturethe reaction mixture was cooled
  2. washwashed three times with water
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography (silica gel, linear gradient 0-75% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-8afcbd229ef94af1a1223a59477f9308
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637513B2

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