Boron tribromide → 5-Amino-4'-fluoro-7'-(2-fluoropyridin-3-yl)-2,6-dihydrospiro[[1,4]oxazine-3,9'-xanthen]-2'-ol

HRID 455641Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 455641
[F:1][C:2]1[C:15]2[O:14][C:13]3[C:8](=[CH:9][C:10]([C:16]4[C:17]([F:22])=[N:18][CH:19]=[CH:20][CH:21]=4)=[CH:11][CH:12]=3)[C:7]3([N:27]=[C:26]([NH2:28])[CH2:25][O:24][CH2:23]3)[C:6]=2[CH:5]=[C:4]([O:29]C)[CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[NH2:28][C:26]1[CH2:25][O:24][CH2:23][C:7]2([C:6]3[CH:5]=[C:4]([OH:29])[CH:3]=[C:2]([F:1])[C:15]=3[O:14][C:13]3[C:8]2=[CH:9][C:10]([C:16]2[C:17]([F:22])=[N:18][CH:19]=[CH:20][CH:21]=2)=[CH:11][CH:12]=3)[N:27]=1

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 674375114'-Fluoro-7'-(2-fluoropyridin-3-yl)-2'-methoxy-2,6-dihydrospiro[[1,4]oxazine-3,9'-xanthen]-5-amine

Produkt 1

HCID 674401225-Amino-4'-fluoro-7'-(2-fluoropyridin-3-yl)-2,6-dihydrospiro[[1,4]oxazine-3,9'-xanthen]-2'-olAusbeute 95,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a suspension of 4′-fluoro-7′-(2-fluoropyridin-3-yl)-2′-methoxy-2,6-dihydrospiro[[1,4]oxazine-3,9′-xanthen]-5-amine (1.668 g, 4.07 mmol) in DCM (12 ml) was added boron tribromide (0.963 mL, 10.19 mmol) at 0° C. The reaction mixture was stirred for 45 hrs at 0° C. The reaction mixture was allowed to warm to RT and was stirred for additional 2 hrs. The reaction mixture was cooled to 0° C. and quenched by addition of saturated aqueous NaHCO3 solution (˜10 mL). The solvent was removed in vacuo, the mixture was diluted with water and filtered. The solid was washed with water and dried under reduced pressure to afford 5-amino-4′-fluoro-7′-(2-fluoropyridin-3-yl)-2,6-dihydrospiro[[1,4]oxazine-3,9′-xanthen]-2′-ol (1.53 g, 3.87 mmol, 95% yield).

Aufarbeitung

  1. temperatureto warm to RT
  2. stirringwas stirred for additional 2 hrs
  3. temperatureThe reaction mixture was cooled to 0° C.
  4. customquenched by addition of saturated aqueous NaHCO3 solution (˜10 mL)
  5. customThe solvent was removed in vacuo
  6. additionthe mixture was diluted with water
  7. filtrationfiltered
  8. washThe solid was washed with water
  9. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b8a02fa966404a538cdc27cf936046e8
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08497264B2

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