Sodium Carbonate → HCID 22872654, Verbindung

HRID 1780347Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1780347
Br[C:2]1[CH:3]=[C:4]([O:9][CH2:10][C@H:11]2[CH2:15][CH2:14][CH2:13][N:12]2[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:5]=[N:6][C:7]=1[Cl:8].[NH2:23][C:24]1[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][CH:29]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1>[NH2:23][C:24]1[CH:29]=[C:28]([C:2]2[CH:3]=[C:4]([O:9][CH2:10][C@H:11]3[CH2:15][CH2:14][CH2:13][N:12]3[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:5]=[N:6][C:7]=2[Cl:8])[CH:27]=[CH:26][CH:25]=1

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 922693-Aminophenylboronic acidHCID 22872666HCID 22872666, Verbindung

Produkt 1

HCID 22872654HCID 22872654, VerbindungAusbeute 29,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of 5-bromo-6-chloro-3-(1-BOC-2-(R)-pyrrolidinylmethoxy)pyridine from Example 69a (520 mg, 1.33 mmol) and 3-aminophenylboronic acid (310 mg, 2.0 mmol) in toluene (8mL) was added Pd(0) (50 mg) and Na2CO3 (2.5 mL of a 2M solution), and the mixture was heated at reflux for 16 hours. The solvent was removed under vacuum, and the residue was purified by chromatography on a silica gel column, eluting with chloroform:ether 100:5-100:4 to afford 160 mg of the title compound. MS (DCI/NH3) m/z 404 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ1.44 (s, 9H), 1.88 (m, 1H), 2.03 (m, 2H), 3.37 (m, 2H), 3.76 (m, 2H), 4.16 (m, 2H), 6.75 (m, 2H), 6.82 (m, 1H), 7.22 (m, 2H), 8.08 (m, 1H).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 16 hours
  3. customThe solvent was removed under vacuum
  4. customthe residue was purified by chromatography on a silica gel column
  5. washeluting with chloroform:ether 100:5-100:4

Quellen und Nachweise

ORD-Eintrag
ord-574ee3e32f7a4c6aa0f7f50fbaeb60eb
Quelldatensatz
uspto-grants-1997_05
Patentnummer
US05629325

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