Cesium carbonate → HCID 58292764, Verbindung

HRID 1798170Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1798170
[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([OH:12])[CH:9]=[C:10]([CH3:11])[C:5]=2[CH:4]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[O:3]1.[Cl:19][C:20]1[CH:25]=[CH:24][N:23]=[C:22]([N+]([O-])=O)[CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Cl:19][C:20]1[CH:25]=[CH:24][N:23]=[C:22]([O:12][C:8]2[CH:9]=[C:10]([CH3:11])[C:5]3[CH:4]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[O:3][B:2]([OH:1])[C:6]=3[CH:7]=2)[CH:21]=1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 27628474-Chloro-2-nitropyridineHCID 58292549Ethyl 2-(1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate

Produkt 1

HCID 58292764HCID 58292764, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of ethyl 2-(1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (2 g, 8 mmol, 1 eq.) and 4-chloro-2-nitropyridine (2.53 g, 16 mmol, 2 eq.) in 50 ml DMF was added cesium carbonate (7.8 g, 24 mmol, 3 eq.). The reaction was stirred at room temperature overnight. It was then quenched by water, extracted with EtOAc, washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The crude was purified by column chromatography on silica gel (DCM/methanol=19:1 to 4:1) to give desired product as light yellow oil. MS (ESI) m/z=721 [2M−H]+.

Aufarbeitung

  1. customIt was then quenched by water
  2. extractionextracted with EtOAc
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe crude was purified by column chromatography on silica gel (DCM/methanol=19:1 to 4:1)

Quellen und Nachweise

ORD-Eintrag
ord-63da6a1ab927476d864161f8e85dfbc0
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08343944B2

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