Water → 6-(Tert-butylthio)methyl-pyridine-3-carbonitrile

HRID 1190967Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1190967
Br[CH2:2][C:3]1[N:8]=[CH:7][C:6]([C:9]#[N:10])=[CH:5][CH:4]=1.[CH3:11][C:12]([SH:15])([CH3:14])[CH3:13].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C.C(Cl)Cl>[C:12]([S:15][CH2:2][C:3]1[N:8]=[CH:7][C:6]([C:9]#[N:10])=[CH:5][CH:4]=1)([CH3:14])([CH3:13])[CH3:11]

Komponenten

7

Edukt 4

HCID 962WaterHCID 6387tert-Butyl mercaptanHCID 10796Cesium carbonateHCID 219277766-(Bromomethyl)pyridine-3-carbonitrile

Produkt 1

HCID 584955036-(Tert-butylthio)methyl-pyridine-3-carbonitrileAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Dissolve 6-bromomethyl-pyridine-3-carbonitrile (6.2 g, 31.4 mmol) in anhydrous DMF (60 mL) under nitrogen. Add tert-butylthiol (5.32 mL, 47.2 mmol) followed by cesium carbonate (15.3 g, 47.2 mmol) and stir the resulting suspension overnight. Dissolve the reaction mixture in DCM (200 mL) and add water (200 mL). Extract the aqueous phase with DCM (2×200 mL) and dry the combined organic extracts over MgSO4. Filter, add silica gel and concentrate the mixture in vacuo. Purify the residue by chromatography on silica gel (40 g) eluting with cyclohexane/EtOAc (98:2 to 65:35 gradient) to obtain the desired material as a yellow solid (4.92 g, 76%). MS (ES+) m/z: 207 (M+H)+.

Aufarbeitung

  1. extractionExtract the aqueous phase with DCM (2×200 mL)
  2. dry with materialdry the combined organic extracts over MgSO4
  3. filtrationFilter
  4. additionadd silica gel
  5. concentrationconcentrate the mixture in vacuo
  6. customPurify the residue by chromatography on silica gel (40 g)
  7. washeluting with cyclohexane/EtOAc (98:2 to 65:35 gradient)

Quellen und Nachweise

ORD-Eintrag
ord-c31941f3b78f4f8c88108a028e0da764
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08680091B2

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