Bromine → Tert-butyl {5-[(2-amino[1,3]thiazolo[5,4-b]pyridin-5-yl)oxy]-2-fluorophenyl}carbamate

HRID 2366785Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2366785
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[CH:10]=[CH:11][C:12]([F:23])=[C:13]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH:14]=2)=[N:6][CH:7]=1.[S-:24][C:25]#[N:26].[K+].BrBr>C(O)(=O)C>[C:18]([O:17][C:16](=[O:22])[NH:15][C:13]1[CH:14]=[C:9]([O:8][C:5]2[N:6]=[C:7]3[S:24][C:25]([NH2:26])=[N:1][C:2]3=[CH:3][CH:4]=2)[CH:10]=[CH:11][C:12]=1[F:23])([CH3:19])([CH3:20])[CH3:21]

Komponenten

5

Edukt 3

HCID 24408BromineHCID 516872Potassium thiocyanateHCID 86657970Tert-butyl {5-[(5-aminopyridin-2-yl)oxy]-2-fluorophenyl}carbamate

Produkt 1

HCID 86657972Tert-butyl {5-[(2-amino[1,3]thiazolo[5,4-b]pyridin-5-yl)oxy]-2-fluorophenyl}carbamateAusbeute 90,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl {5-[(5-aminopyridin-2-yl)oxy]-2-fluorophenyl}carbamate (3.00 g, 9.4 mmol) and potassium thiocyanate (3.93 g, 40 mmol) in acetic acid (40 mL) was added dropwise bromine (2.40 g, 15 mmol) under ice-cooling, and the mixture was stirred at room temperature overnight. The yellow insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. Saturated aqueous sodium hydrogen carbonate solution (200 mL) was added to the residue, and the mixture was extracted with ethyl acetate (100 mL×2). The ethyl acetate layers were combined and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was triturated with diethyl ether to give the title compound (3.20 g, 90%) as a pale-yellow powder.

Aufarbeitung

  1. temperaturecooling
  2. filtrationThe yellow insoluble material was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionSaturated aqueous sodium hydrogen carbonate solution (200 mL) was added to the residue
  5. extractionthe mixture was extracted with ethyl acetate (100 mL×2)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationThe insoluble material was filtered off
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe obtained residue was triturated with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-e6f5acc7e9f84439b40282bff777c952
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08697874B2

Notizen zur Reaktion

Wird geladen…