Boron tribromide → 2-(7-Amino-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-phenol

HRID 1802274Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1802274
C[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:18]=[C:12]2[CH:13]=[C:14]([NH2:17])[CH:15]=[CH:16][N:11]2[N:10]=1.B(Br)(Br)Br>C(Cl)Cl>[NH2:17][C:14]1[CH:15]=[CH:16][N:11]2[N:10]=[C:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[OH:2])[N:18]=[C:12]2[CH:13]=1

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 677742602-(2-Methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-amine

Produkt 1

HCID 1363723582-(7-Amino-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-phenolAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a solution of 2-(2-methoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-ylamine (2.3 g, 9.6 mmol) (Example 102, step c) in DCM (60 ml) was added a solution of BBr3 (1 M in DCM, 28.7 ml, 28.7 mmol). The mixture was allowed to warm up to 25° C. and stirring was continued for 2 h. Volatiles were removed under reduced pressure and the crude residue was extracted with DCM and washed with aq. NaHCO3 solution. The organic layer was washed with brine, dried over Na2SO4 and concentrated to get the crude product which was washed with 10% DCM in hexane to afford the title compound as off-white solid (1.3 g, 60%). LC-MS: m/z=227.4 [M+H]+.

Aufarbeitung

  1. customVolatiles were removed under reduced pressure
  2. extractionthe crude residue was extracted with DCM
  3. washwashed with aq. NaHCO3 solution
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customto get the crude product which
  8. washwas washed with 10% DCM in hexane

Quellen und Nachweise

ORD-Eintrag
ord-89327fe6c6de412b9fb37259b93d66bf
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08349824B2

Notizen zur Reaktion

Wird geladen…