Sodium hydride → HCID 9967206, Verbindung

HRID 8247Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 8247
[OH:1][CH2:2][CH2:3][N:4]1[C:8]([CH2:9]O)=[C:7]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=[CH:13][CH:12]=2)[C:6]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)=[N:5]1.[H-].[Na+].CS(Cl)(=O)=O>O1CCCC1>[N:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[C:6]1[C:7]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=[CH:13][CH:12]=2)=[C:8]2[CH2:9][O:1][CH2:2][CH2:3][N:4]2[N:5]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 219926122-(2-Hydroxyethyl)-3-hydroxymethyl-5-pyridin-2-yl-4-quinolin-4-yl-pyrazole

Produkt 1

HCID 9967206HCID 9967206, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 2-(2-hydroxyethyl)-3-hydroxymethyl-5-pyridin-2-yl-4-quinoline-4-yl-pyrazole, (0.10 g, 0.29 mmol) in tetrahydrofuran (10 mL) cooled at 0° C. is added NaH (0.04 g, 50% in mineral oil). The mixture is stirred for 2 h at room temperature and methanesulfonyl chloride (0.065 g, 0.57 mmol) is added dropwise over 30 min. The reaction is quenched with water and extracted into ethyl acetate. The organic layer is washed with water, dried (sodium sulfate), filtered, and concentrated in vacuo. The residue is chromatographed on SiO2 (10% methanol/dichloromethane) to yield the title compound, 31 mg (33%), as a white solid.

Aufarbeitung

  1. customThe reaction is quenched with water
  2. extractionextracted into ethyl acetate
  3. washThe organic layer is washed with water
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is chromatographed on SiO2 (10% methanol/dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-be7a79edca974d11a6f6a3374a17c190
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087626B2

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