Boron tribromide → HCID 59436049, Verbindung

HRID 1802488Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1802488
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[C:3]=1[NH:10][C:11]1[C:20]2[CH:21]=[CH:22][N:23]=[C:24]([O:25]CC)[C:19]=2[C:18]2[C:13](=[CH:14][CH:15]=[N:16][CH:17]=2)[N:12]=1.ClC1C2C3C(=CC=NC=3)N=C(NC3C(F)=CC(F)=CC=3Cl)C=2C=CN=1.C[O-].[Na+].B(Br)(Br)Br>CO>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[C:3]=1[NH:10][C:11]1[C:20]2[CH:21]=[CH:22][NH:23][C:24](=[O:25])[C:19]=2[C:18]2[C:13](=[CH:14][CH:15]=[N:16][CH:17]=2)[N:12]=1

Komponenten

6

Edukt 4

HCID 25134Boron tribromideHCID 10942334Sodium MethoxideHCID 59436014HCID 59436014, VerbindungHCID 59436106HCID 59436106, Verbindung

Produkt 1

HCID 59436049HCID 59436049, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of N-(2-chloro-4,6-difluorophenyl)-10-ethoxypyrido[4,3-c]-1,6-naphthyridin-6-amine and 10-chloro-N-(2-chloro-4,6-difluorophenyl)pyrido[4,3-c]-1,6-naphthyridin-6-amine (1.3 g) in 8 mL methanol was added sodium methoxide (5 mL, 2.06 mmol, 25% weight in methanol) and the mixture was heated to 100° C. for 1 hr. The solution was cooled to room temperature, concentrated, and redissolved with 3:1 CHCl3/i-PrOH followed by a wash with saturated NH4Cl. The organic layers were combined, dried with MgSO4, filtered, and concentrated under reduced pressure. A portion of the crude solution (540 mg) was taken up in CHCl3 (8 mL) and boron tribromide (1M in CH2Cl2, 7 mL, 7.0 mmol) and heated to 85° C. for 1 hr. The solution was cooled to room temperature, extracted with 3:1 CHCl3/i-PrOH, and washed with saturated NaHCO3. The organic layers were dried with MgSO4, filtered, and concentrated to afford the crude product. The crude residue was purified on silica gel (100% CH2Cl2 to 25% MeOH, gradient elution) which afforded the title compound.

Aufarbeitung

  1. temperatureThe solution was cooled to room temperature
  2. concentrationconcentrated
  3. dissolutionredissolved with 3:1 CHCl3/i-PrOH
  4. washa wash with saturated NH4Cl
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. temperatureThe solution was cooled to room temperature
  9. extractionextracted with 3:1 CHCl3/i-PrOH
  10. washwashed with saturated NaHCO3
  11. dry with materialThe organic layers were dried with MgSO4
  12. filtrationfiltered
  13. concentrationconcentrated
  14. customto afford the crude product
  15. customThe crude residue was purified on silica gel (100% CH2Cl2 to 25% MeOH, gradient elution) which

Quellen und Nachweise

ORD-Eintrag
ord-0f8cc2bc16d14e43826db59610443758
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08349865B2

Notizen zur Reaktion

Wird geladen…