Ammonium Chloride → tert-butyl N-(3-bromo-6-methylpyrazolo[5,1-b][1,3]thiazol-7-yl)carbamate

HRID 41259

Reaktionsgleichung

Reaktionsgleichung von HRID 41259
[C:1]([O:5][C:6](=[O:17])[NH:7][C:8]1[C:9]([CH3:16])=[N:10][N:11]2[CH:15]=[CH:14][S:13][C:12]=12)([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.[Br:23]C(F)(F)C(F)(F)Br.[Cl-].[NH4+]>O1CCCC1>[C:1]([O:5][C:6](=[O:17])[NH:7][C:8]1[C:9]([CH3:16])=[N:10][N:11]2[C:15]([Br:23])=[CH:14][S:13][C:12]=12)([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 25517Ammonium ChlorideHCID 313011,2-Dibromo-1,1,2,2-tetrafluoroethaneHCID 58223383tert-butyl N-(6-methylpyrazolo[5,1-b][1,3]thiazol-7-yl)carbamateHCID 178418339Butyllithium

Produkt 1

HCID 58223433tert-butyl N-(3-bromo-6-methylpyrazolo[5,1-b][1,3]thiazol-7-yl)carbamateAusbeute 91,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A tetrahydrofuran (40 mL) solution of tert-butyl(6-methylpyrazolo[5,1-b][1,3]thiazol-7-yl)carbamate (1.20 g, 4.74 mmol) was cooled to −78° C., and n-butyllithium (1.57 M, 6.64 mL, 10.4 mmol) was added dropwise thereto, and the mixture was stirred for 30 minutes. Then, 1,2-dibromotetrafluoroethane (619 μl, 5.21 mmol) was added to the mixture, and the reaction mixture was warmed to room temperature, and stirred at room temperature for one hour. To the reaction mixture, a saturated aqueous solution of ammonium chloride was added, and a substance of interest was extracted with ethyl acetate. The organic layer was washed with brine and dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by medium pressure silica gel column chromatography (n-heptane/ethyl acetate: 50% then 66%) to obtain 1.39 g (4.32 mmol) of the title compound.

Aufarbeitung

  1. stirringstirred at room temperature for one hour
  2. extractiona substance of interest was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by medium pressure silica gel column chromatography (n-heptane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-c649c0deb82342c1a33eb64dc231f13d
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530504B2

Verknüpfte Notizen

Wird geladen…