Reaktionsgleichung
[F:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[CH:12]([OH:15])[CH2:13][OH:14])=[N:9][C:8]([O:16][CH3:17])=[CH:7][CH:6]=2.C(N(CC)CC)C.[S:25](Cl)([C:28]1[CH:34]=[CH:33][C:31]([CH3:32])=[CH:30][CH:29]=1)(=[O:27])=[O:26]>ClCCl.O.C(=O)(O)[O-].[Na+].C([Sn](=O)CCCC)CCC>[CH3:32][C:31]1[CH:33]=[CH:34][C:28]([S:25]([O:14][CH2:13][CH:12]([C:11]2[C:10]3[C:5](=[CH:6][CH:7]=[C:8]([O:16][CH3:17])[N:9]=3)[N:4]=[CH:3][C:2]=2[F:1])[OH:15])(=[O:27])=[O:26])=[CH:29][CH:30]=1Komponenten
7
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Versuchsvorschrift
To a solution of 1-[3-fluoro-6-(methoxy)-1,5-naphthyridin-4-yl]-1,2-ethanediol (16.5 g, 71 mmol)) in dichloromethane (200 mL), triethylamine (10 mL) and dibutyltin oxide (350 mg) was added tosyl chloride (13.2 g). After 3 hours, the mixture was diluted with water/sodium bicarbonate and extracted several times with chloroform. The combined organic extracts were dried over magnesium sulfate and evaporated under vacuum. The residue was chromatographed on silica gel eluting with 20-30% ethyl acetate in chloroform to afford the desired product (20.3 g, 75%). MS (+ve ion electrospray) m/z 393 (M+H)+.
Aufarbeitung
- extractionextracted several times with chloroform
- dry with materialThe combined organic extracts were dried over magnesium sulfate
- customevaporated under vacuum
- customThe residue was chromatographed on silica gel eluting with 20-30% ethyl acetate in chloroform
Quellen und Nachweise
- ORD-Eintrag
- ord-a24824a6d8f6436ba773bee0138d6b6d
- Quelldatensatz
- uspto-grants-2010_04
- Patentnummer
- US07691850B2
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