Cesium carbonate → 5-Chloro-2-{[4-(methylsulfonyl)phenyl]oxy}pyridine

HRID 32384

Reaktionsgleichung

Reaktionsgleichung von HRID 32384
Cl[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1.[CH3:9][S:10]([C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)(=[O:12])=[O:11].C([O-])([O-])=O.[Cs+].[Cs+]>CN1C(=O)CCC1>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([O:19][C:16]2[CH:15]=[CH:14][C:13]([S:10]([CH3:9])(=[O:12])=[O:11])=[CH:18][CH:17]=2)=[N:3][CH:4]=1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonate2×HCID 276852,5-DichloropyridineHCID 1233504-(Methylsulfonyl)phenol

Produkt 1

HCID 231335105-Chloro-2-{[4-(methylsulfonyl)phenyl]oxy}pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
170 °C

Versuchsvorschrift

2,5-dichloropyridine (1.48 g; 10 mmol), 4-methylsulfonylphenol (1.89 g; 11 mmol) and Cs2CO3 (4.24 g; 13 mmol) was slurried in 75 mL of NMP. The slurry was heated to approx 170° C. over night. After cooling the Cs2CO3 was filtered off and the solvent was extracted between H2O and EtOAc. The organic phase was dried over Na2SO4 and evaporated. Heptane:EtOAc 2:1 was added to the residue and the crystalls was filtered off 1.42 g (50%).

Aufarbeitung

  1. filtrationwas filtered off
  2. extractionthe solvent was extracted between H2O and EtOAc
  3. dry with materialThe organic phase was dried over Na2SO4
  4. customevaporated
  5. additionHeptane:EtOAc 2:1 was added to the residue
  6. filtrationthe crystalls was filtered off 1.42 g (50%)

Quellen und Nachweise

ORD-Eintrag
ord-b538d16793344b958f75b279f78671ff
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07427631B2

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