Sodium Carbonate → HCID 22872657, Verbindung

HRID 1780348Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1780348
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].[Cl:23][C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1>[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([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:26][CH:25]=1

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 22872666HCID 22872666, Verbindung

Produkt 1

HCID 22872657HCID 22872657, VerbindungAusbeute 68 %

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 (460 mg, 1.2 mmol) and 4-chlorophenylboronic acid (225 mg, 1.44 mmol) in toluene (10 mL) was added Pd(0) (40 mg) and Na2CO3 (1.2 mL of a 2M solution), and the mixture was heated at reflux for 1.5 hours. The solvent was removed under vacuum, and the residue was purified by chromotography on a silica gel column, eluting with hexane:ether 100:10-100:30 to afford of the title compound (345 mg, 68% yield). MS (DCI/NH3) m/z 423 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ1.45 (s, 9H), 1.89 (m, 2H), 2.03 (m, 2H), 3.37 (m, 2H), 4.00 (m, 1H), 4.15 (m, 2H), 7.42 (m, 6H), 8.10 (m, 2H).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 1.5 hours
  3. customThe solvent was removed under vacuum
  4. customthe residue was purified by chromotography on a silica gel column
  5. washeluting with hexane:ether 100:10-100:30

Quellen und Nachweise

ORD-Eintrag
ord-c25a76b8f7dd4aa79d706844ddabe8bf
Quelldatensatz
uspto-grants-1997_05
Patentnummer
US05629325

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