Water → 2-((9-amino-7-bromo-4-fluoro-2-methoxy-9H-xanthen-9-yl)methoxy)acetonitrile

HRID 455572Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 455572
[NH2:1][C:2]1([CH2:20][OH:21])[C:15]2[CH:14]=[C:13]([O:16][CH3:17])[CH:12]=[C:11]([F:18])[C:10]=2[O:9][C:8]2[C:3]1=[CH:4][C:5]([Br:19])=[CH:6][CH:7]=2.CC(C)([O-])C.[Li+].Br[CH2:29][C:30]#[N:31].O>C1COCC1>[NH2:1][C:2]1([CH2:20][O:21][CH2:29][C:30]#[N:31])[C:15]2[CH:14]=[C:13]([O:16][CH3:17])[CH:12]=[C:11]([F:18])[C:10]=2[O:9][C:8]2[C:3]1=[CH:4][C:5]([Br:19])=[CH:6][CH:7]=2

Komponenten

6

Edukt 4

HCID 962WaterHCID 11534Bromoacetonitrile4×HCID 236647642-Propanol, 2-methyl-, lithium salt (1:1)4×HCID 67383452(9-amino-7-bromo-4-fluoro-2-methoxy-9H-xanthen-9-yl)methanol

Produkt 1

HCID 673828282-((9-amino-7-bromo-4-fluoro-2-methoxy-9H-xanthen-9-yl)methoxy)acetonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of (9-amino-7-bromo-4-fluoro-2-methoxy-9H-xanthen-9-yl)methanol (9.83 g, 27.8 mmol) in THF (46.3 mL) was sequentially treated with lithium t-butoxide (1 M in THF) (30.5 mL, 30.5 mmol) and 2-bromoacetonitrile (2.90 mL, 41.6 mmol) at RT. After 2.5 hours reaction time, additional 0.5 equivalent lithium t-butoxide and 2-bromoacetonitrile (1.5 mL) were added. After 4 hours reaction time, an additional 0.25 equivalent lithium t-butoxide and bromoacetonitrile (0.75 mL) were added. After 5 hours reaction time another 0.25 equivalent of lithium t-butoxide and bromoacetonitrile (0.75 mL) were added to the mixture. Water (100 ml) was added and solvents were removed under reduced pressure. The aqueous residue was filtered, the solid was washed twice with water, dried under reduced pressure and re-suspended in ethanol. The solid was filtered off, washed with ethanol and dried under reduced pressure to afford 2-((9-amino-7-bromo-4-fluoro-2-methoxy-9H-xanthen-9-yl)methoxy)acetonitrile.

Aufarbeitung

  1. additionwere added
  2. customAfter 4 hours reaction time
  3. additionwere added to the mixture
  4. customsolvents were removed under reduced pressure
  5. filtrationThe aqueous residue was filtered
  6. washthe solid was washed twice with water
  7. customdried under reduced pressure
  8. filtrationThe solid was filtered off
  9. washwashed with ethanol
  10. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-815140bcc91048b48c9e712d64879f42
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08497264B2

Notizen zur Reaktion

Wird geladen…