Lithium Hexamethyldisilazide → 5-fluoro-2-(2-fluoro-4-(methylthio)phenylamino)-1-methyl-6-oxo-N-(2-(vinyloxy)ethoxy)-1,6-dihydropyridine-3-carboxamide

HRID 15982

Reaktionsgleichung

Reaktionsgleichung von HRID 15982
[F:1][C:2]1[C:7](=[O:8])[N:6]([CH3:9])[C:5]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([S:17][CH3:18])=[CH:13][C:12]=2[F:19])=[C:4]([C:20]([O:22]C)=O)[CH:3]=1.[CH:24]([O:26][CH2:27][CH2:28][O:29][NH2:30])=[CH2:25].C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>C1COCC1>[F:1][C:2]1[C:7](=[O:8])[N:6]([CH3:9])[C:5]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([S:17][CH3:18])=[CH:13][C:12]=2[F:19])=[C:4]([C:20]([NH:30][O:29][CH2:28][CH2:27][O:26][CH:24]=[CH2:25])=[O:22])[CH:3]=1

Komponenten

5

Edukt 3

HCID 2733832Lithium HexamethyldisilazideHCID 21867017O-(2-(Vinyloxy)ethyl)hydroxylamineHCID 66673936Methyl 5-fluoro-2-(2-fluoro-4-(methylthio)phenylamino)-1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylate

Produkt 1

HCID 866125345-fluoro-2-(2-fluoro-4-(methylthio)phenylamino)-1-methyl-6-oxo-N-(2-(vinyloxy)ethoxy)-1,6-dihydropyridine-3-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of methyl 5-fluoro-2-(2-fluoro-4-(methylthio)phenylamino)-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate (0.100 g, 0.294 mmol) and O-(2-(vinyloxy)ethyl)hydroxylamine (0.045 ml, 0.441 mmol) in THF (2 mL) at 0° C. was added lithium bis(trimethylsilyl)amide (1.18 ml, 1.18 mmol, 1 M solution in hexanes) dropwise. The reaction mixture was stirred for 20 minutes, quenched with 1 M HCl, and then partitioned between EtOAc and sat NaCl. The layers were separated and the aqueous layer was backextracted with EtOAc (1×). The combined organic layers were dried (Na2SO4), filtered and concentrated under reduced pressure to yield a crude yellow solid that was used without purification in the next step.

Aufarbeitung

  1. customquenched with 1 M HCl
  2. custompartitioned between EtOAc
  3. customThe layers were separated
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto yield a crude yellow solid that
  8. customwas used without purification in the next step

Quellen und Nachweise

ORD-Eintrag
ord-b9b94b3733a74cc9974263223fb72f18
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732616B2

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