Sodium Bicarbonate → HCID 18396219, Verbindung

HRID 611592

Reaktionsgleichung

Reaktionsgleichung von HRID 611592
[C:1]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[C:13]1[O:21][C:20]2[C:15](=[N:16][C:17]([Cl:23])=[C:18](Br)[CH:19]=2)[CH:14]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[NH2:24][C:25]1[CH:26]=[C:27](OB(O)O)[CH:28]=[CH:29][CH:30]=1.C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1>[C:1]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[C:13]1[O:21][C:20]2[C:15](=[N:16][C:17]([Cl:23])=[C:18]([C:29]3[CH:28]=[CH:27][CH:26]=[C:25]([NH2:24])[CH:30]=3)[CH:19]=2)[CH:14]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 18396220HCID 18396220, VerbindungHCID 218958363-Aminophenylboric acid

Produkt 1

HCID 18396219HCID 18396219, VerbindungAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

The 2-(1-Boc-2-(R)-pyrrolidinyl)-5-chloro-6-bromo furo[3,2-b]pyridine (0.469 g, 1.2 mmol), obtained in Example 50a above, was dissolved in toluene (10 mL). 3-Aminophenyl boric acid (0.445 g, 2.87 mmol), Pd(O) tetrakis(tri-phenylphosphine) (0.04 g) and 2 M aqueous NaHCO3 (1.5 mL) were added to the solution. The mixture was refluxed for two days. The solvent was evaporated and the residue was chromatographed (silica gel; hexane/EtOAc, 5:1 to 2:1) to afford an oil (0.20 g, 41%). MS (CI/NH3) m/z: 414 (M+H)+ ; 1H NMR (CDCl3, 300 MHz) δ 1.34, 1.46 (s, 9H), 1.95-2.08 (m, 2H), 2.15 (m, 1H), 2.28 (m, 1H), 3.58-3.68 (m, 2H), 4.98, 5.10 (br s, 1H), 6.24 (m, 1H), 6.63 (s, 1H) 6.76 (d, J=9.3 Hz, 2H), 6.82 (d, J=9.3 Hz, 1H) 7.62 (s, 1H).

Aufarbeitung

  1. temperatureThe mixture was refluxed for two days
  2. customThe solvent was evaporated
  3. customthe residue was chromatographed (silica gel; hexane/EtOAc, 5:1 to 2:1)

Quellen und Nachweise

ORD-Eintrag
ord-782339096a734d359168efc3c2aecc4e
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US06001849

Verknüpfte Notizen

Wird geladen…