Boron tribromide → 1-[4-(2-Fluorophenyl)-1,3-thiazol-2-yl]piperazine

HRID 1361475Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1361475
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[C:10]([N:13]2[CH2:18][CH2:17][N:16](C(OCC3C=CC=CC=3)=O)[CH2:15][CH2:14]2)[S:11][CH:12]=1.B(Br)(Br)Br>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[C:10]([N:13]2[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]2)[S:11][CH:12]=1

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 15984569Benzyl 4-(4-(2-fluorophenyl)thiazol-2-yl)piperazine-1-carboxylate

Produkt 1

HCID 581827331-[4-(2-Fluorophenyl)-1,3-thiazol-2-yl]piperazine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-50 °C

Versuchsvorschrift

To a solution of benzyl 4-(4-(2-fluorophenyl)thiazol-2-yl)piperazine-1-carboxylate (0.85 g, 2.1 mmol) in CH2Cl2 (2 μL) cooled to −50° C. was added boron tribromide (1 M in CH2Cl2, 8.6 mL, 8.6 mmol). The reaction was stirred at −50° C. for 20 min and then carefully quenched with saturated aqueous NaHCO3. The mixture was extracted with CH2Cl2, and the combined extracts were washed with water, dried over Na2SO4, and concentrated under reduced pressure to yield 1-(4-(2-fluorophenyl)thiazol-2-yl)piperazine. LC/MS: m/z 264.1 (M+H)+ at 2.04 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Aufarbeitung

  1. customcarefully quenched with saturated aqueous NaHCO3
  2. extractionThe mixture was extracted with CH2Cl2
  3. washthe combined extracts were washed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3f60637d4abd47f99a648cf971372941
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07880008B2

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