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Cesium carbonate → HCID 21084058, Verbindung

HRID 347917
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 347917
Br[CH2:2][CH2:3][OH:4].[OH:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:17](=[O:18])[CH:16]=[CH:15][C:14]3[C:19]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[C:20]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[S:21][C:13]2=3)=[CH:8][CH:7]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[OH:4][CH2:3][CH2:2][O:5][C:6]1[CH:7]=[CH:8][C:9]([N:12]2[C:17](=[O:18])[CH:16]=[CH:15][C:14]3[C:19]([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)=[C:20]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[S:21][C:13]2=3)=[CH:10][CH:11]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 108982-BromoethanolHCID 21084070HCID 21084070, Verbindung

Produkt 1

HCID 21084058HCID 21084058, VerbindungAusbeute 18 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2-Bromoethanol (0.148 mL, 2.08 mmol) was added to the compound of Example 89 (370 mg, 0.95 mmol) and Cs2CO3 (342 mg, 1.04 mmol) in DMF (5 mL) and the mixture heated at 80° for 2 days. The solvent was removed in vacuo and the residue partitioned between EtOAc and HCl (10%). The aqueous phase was extracted with EtOAc (2×20 mL). The combined organics were washed with brine, dried (MgSO4) and concentrated in vacuo. The crude product was purified by column chromatography on silica (2% to 10% MeOH in DCM) to give the title compound (73 mg, 18%). δH (CDCl3) 7.44–7.28 (8H, m), 7.07 (2H, d, J 8 Hz), 6.52 (1H, d, J 9.6 Hz), 4.12–3.93 (6H, m), 1.06 (3H, t, J 7.1 Hz). LCMS (ES+) RT 3.42 minutes, 436 (M+H)+.

Aufarbeitung

  1. temperaturethe mixture heated at 80° for 2 days
  2. customThe solvent was removed in vacuo
  3. customthe residue partitioned between EtOAc and HCl (10%)
  4. extractionThe aqueous phase was extracted with EtOAc (2×20 mL)
  5. washThe combined organics were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by column chromatography on silica (2% to 10% MeOH in DCM)

Quellen und Nachweise

ORD-Eintrag
ord-d63f28bed48846dc9fe2aaa5fee7b358
Quelldatensatz
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07176215B2

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