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Sodium bis(trimethylsilyl)amide → 4-[(6-tert-butoxy-5-chloropyridin-3-yl)oxy]-5-chloro-2-fluoro-N-(methylsulfonyl)benzamide

HRID 2048031
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2048031
FC1(F)CC(C([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=O)C1.C[Si](C)(C)[N-][Si](C)(C)C.[Na+].[Cl:24][C:25]1[C:26]([O:39][C:40]2[CH:41]=[N:42][C:43](F)=[C:44]([Cl:46])[CH:45]=2)=[CH:27][C:28]([F:38])=[C:29]([CH:37]=1)[C:30]([NH:32][S:33]([CH3:36])(=[O:35])=[O:34])=[O:31]>C1(C)C=CC=CC=1>[C:9]([O:8][C:43]1[N:42]=[CH:41][C:40]([O:39][C:26]2[C:25]([Cl:24])=[CH:37][C:29]([C:30]([NH:32][S:33]([CH3:36])(=[O:35])=[O:34])=[O:31])=[C:28]([F:38])[CH:27]=2)=[CH:45][C:44]=1[Cl:46])([CH3:12])([CH3:11])[CH3:10]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 580424375-Chloro-4-[(5-chloro-6-fluoropyridin-3-yl)oxy]-2-fluoro-N-(methylsulfonyl)benzamideHCID 58042504Cyclobutanecarboxylic acid, 3,3-difluoro-, 1,1-dimethylethyl ester

Produkt 1

HCID 580424094-[(6-tert-butoxy-5-chloropyridin-3-yl)oxy]-5-chloro-2-fluoro-N-(methylsulfonyl)benzamideAusbeute 44,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl 3,3-difluorocyclobutanecarboxylate (Preparation 227, 126 mg, 0.66 mmol) in toluene (2 mL) was added a solution of sodium 1,1,1,3,3,3-hexamethyldisilazan-2-ide (1M solution in THF, 1.6 mL, 1.6 mmol) at 0° C. The resulting solution was stirred for 10 minutes at the same temperature, then 5-chloro-4-[(5-chloro-6-fluoropyridin-3-yl)oxy]-2-fluoro-N-(methylsulfonyl)benzamide (Example 19, 200 mg, 0.50 mmol) was added. The resulting mixture was warmed up to room temperature and stirred for 36 hours. The reaction was quenched with saturated aqueous NH4Cl solution and extracted with EtOAc. The organic phase was washed with aqueous 1N citric acid solution, then brine, dried over Na2SO4, filtered, and concentrated in vacuo to give a crude product as a yellow oil. The crude product was purified by silica gel column chromatography eluting with 0-100% EtOAc in heptane to give a yellow foam. The foam was triturated with heptane to give the title compound (101 mg, 44%) as a white solid.

Aufarbeitung

  1. stirringstirred for 36 hours
  2. customThe reaction was quenched with saturated aqueous NH4Cl solution
  3. extractionextracted with EtOAc
  4. washThe organic phase was washed with aqueous 1N citric acid solution
  5. dry with materialbrine, dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a crude product as a yellow oil
  9. customThe crude product was purified by silica gel column chromatography
  10. washeluting with 0-100% EtOAc in heptane
  11. customto give a yellow foam
  12. customThe foam was triturated with heptane

Quellen und Nachweise

ORD-Eintrag
ord-05957889bf644456b36b6e323b1ec333
Quelldatensatz
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08592629B2

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