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

HRID 1800547Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1800547
[C:1]([O:5][C:6](=[O:23])[NH:7][C:8]1[CH:13]=[C:12]([O:14][C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][N:16]=2)[CH:11]=[CH:10][C:9]=1[F:22])([CH3:4])([CH3:3])[CH3:2].[S-:24][C:25]#[N:26].[K+].BrBr>C(O)(=O)C>[C:1]([O:5][C:6](=[O:23])[NH:7][C:8]1[CH:13]=[C:12]([O:14][C:15]2[N:16]=[C:17]3[S:24][C:25]([NH2:26])=[N:21][C:18]3=[CH:19][CH:20]=2)[CH:11]=[CH:10][C:9]=1[F:22])([CH3:4])([CH3:2])[CH3:3]

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. To residue was added saturated aqueous sodium hydrogen carbonate solution (200 mL), 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 amorphous.

Aufarbeitung

  1. temperaturecooling
  2. filtrationThe yellow insoluble material was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionTo residue was added saturated aqueous sodium hydrogen carbonate solution (200 mL)
  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-34188b2d792e46f4a09528e52fed5ed6
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08344135B2

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