Water → 2-Bromo-6-[4-(1-pyrrolidinylmethyl)phenoxy]pyridine

HRID 460215

Reaktionsgleichung

Reaktionsgleichung von HRID 460215
[H-].[Na+].[N:3]1([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[CH2:7][CH2:6][CH2:5][CH2:4]1.[Br:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19](Br)[N:18]=1.O>CN(C=O)C>[Br:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:15][C:12]2[CH:11]=[CH:10][C:9]([CH2:8][N:3]3[CH2:7][CH2:6][CH2:5][CH2:4]3)=[CH:14][CH:13]=2)[N:18]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 122742,6-DibromopyridineHCID 24758Sodium hydrideHCID 187719784-(Pyrrolidin-1-ylmethyl)phenol

Produkt 1

HCID 187716522-Bromo-6-[4-(1-pyrrolidinylmethyl)phenoxy]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirred suspension of NaH (2.6 g, 108.5 mmol) in DMF (300 mL) at 0° C., under N2, a solution of 4-pyrrolidin-1-ylmethylphenol (16 g, 90.4 mmol) was added slowly. After stirring at 0° C. for 30 min, 2,6-dibromopyridine (23.6 g, 99.4 mmol) was added and the resulting mixture was heated at 95° C. for 20 h. After cooling to RT, 200 mL of H2O was added and the mixture was extracted with EtOAc (3×300 mL). The combined organic layer was washed with brine (3×400 mL), dried over MgSO4, filtered and concentrated under reduced pressure to yield the title compound as an amber solid. This was used crude in the next step. MS m/z: 333 (M+1). Calc'd for C16H17BrN2O-333.2

Aufarbeitung

  1. temperaturethe resulting mixture was heated at 95° C. for 20 h
  2. temperatureAfter cooling to RT
  3. extractionthe mixture was extracted with EtOAc (3×300 mL)
  4. washThe combined organic layer was washed with brine (3×400 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-cefd933575fd4c18a2f7015429234586
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07196104B2

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