Cesium carbonate → HCID 68108563, Verbindung

HRID 538392Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 538392
[CH2:1]([O:3][C:4]([C:6]1[N:11]=[C:10]2[CH:12]=[CH:13][NH:14][C:9]2=[CH:8][C:7]=1[Cl:15])=[O:5])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[F:22][CH:23]([F:26])[CH2:24]I.[NH4+].[Cl-]>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:1]([O:3][C:4]([C:6]1[N:11]=[C:10]2[CH:12]=[CH:13][N:14]([CH2:24][CH:23]([F:26])[F:22])[C:9]2=[CH:8][C:7]=1[Cl:15])=[O:5])[CH3:2]

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 25517Ammonium ChlorideHCID 38335651,1-Difluoro-2-iodoethaneHCID 60058581Ethyl 6-chloro-1H-pyrrolo[3,2-B]pyridine-5-carboxylate

Produkt 1

HCID 68108563HCID 68108563, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 6-chloro-1H-pyrrolo[3,2-b]pyridine-5-carboxylic acid ethyl ester (210 mg, 0.935 mmol) in DMF (10 ml) was added cesium carbonate (457 mg, 1.402 mmol), after 15 min stirring at room temperature 1,1-difluoro-2-iodoethane (538 mg, 2.8 mmol) was added and stirring was continued over night. Tetrabutylammonium iodide (34.5 mg, 0.093 mmol) was added and stirring was continued for another 48 h. To the reaction mixture was added saturated aq. NH4Cl and the mixture was extracted with MTBE (2×). The combined organic layers were washed with half-saturated aq. NaCl, dried with Na2SO4 and evaporated. The residue was purified by chromatography on silica gel (cyclohexane to cyclohexane/EtOAc 20:80) to provide the title compound as yellow solid.

Aufarbeitung

  1. additionwas added
  2. waitwas continued over night
  3. stirringstirring
  4. extractionthe mixture was extracted with MTBE (2×)
  5. washThe combined organic layers were washed with half-saturated aq. NaCl
  6. dry with materialdried with Na2SO4
  7. customevaporated
  8. customThe residue was purified by chromatography on silica gel (cyclohexane to cyclohexane/EtOAc 20:80)

Quellen und Nachweise

ORD-Eintrag
ord-1e9443366b3c474481892a221fdb7bbf
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08865712B2

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