Sodium hydride → 5-Bromo-2-(4-cyclohexyl-3-trifluoromethyl-benzyloxy)-pyridine

HRID 2100660

Reaktionsgleichung

[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][OH:14])=[CH:9][C:8]=2[C:15]([F:18])([F:17])[F:16])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].Cl[C:22]1[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][N:23]=1.[NH4+].[Cl-]>CN(C=O)C>[Br:28][C:25]1[CH:26]=[CH:27][C:22]([O:14][CH2:13][C:10]2[CH:11]=[CH:12][C:7]([CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)=[C:8]([C:15]([F:16])([F:17])[F:18])[CH:9]=2)=[N:23][CH:24]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a solution of (4-cyclohexyl-3-trifluoromethyl-phenyl)-methanol (258 mg, 1.0 mmol) in DMF (7 mL) is added sodium hydride (60% in mineral oil, 60 mg, 1.5 mmol) at 0° C. and the reaction mixture is stirred at 0° C. for 30 minutes. After the addition of a solution of 2-chloro-5-bromopyridine (231 mg, 1.2 mmol) in DMF (3 mL), the reaction mixture is stirred at 0° C. for 1 h and at room temperature for 18 hours. The reaction mixture is poured into saturated aqueous NH4Cl and extracted with EtOAc. The combined extracts are washed with brine and dried over Na2SO4. After concentration, the residue is purified by silica gel chromatography (19:1 hexanes/EtOAc) to give 5-Bromo-2-(4-cyclohexyl-3-trifluoromethyl-benzyloxy)-pyridine.

Aufarbeitung

stirringthe reaction mixture is stirred at 0° C. for 1 h and at room temperature for 18 hours
extractionextracted with EtOAc
washThe combined extracts are washed with brine
dry with materialdried over Na2SO4
concentrationAfter concentration
customthe residue is purified by silica gel chromatography (19:1 hexanes/EtOAc)

Quellen und Nachweise

ORD-Eintrag: ord-1e51157896e94935842a7b9792f38800
Quelldatensatz: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07572811B2

Verknüpfte Notizen

Wird geladen…