Cesium carbonate → Tert-butyl 6-(benzenesulfonylmethyl)-3-(2-formylfuran-3-yl)-2-(2-hydroxyacetylamino)-benzoate

HRID 1778357Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1778357
[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[C:15]([NH:24][C:25](=[O:28])[CH2:26][OH:27])[C:14](Br)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:30]([C:32]1[O:33][CH:34]=[CH:35][C:36]=1B1OC(C)(C)C(C)(C)O1)=[O:31].C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1.O.C(OCC)(=O)C>[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[C:15]([NH:24][C:25](=[O:28])[CH2:26][OH:27])[C:14]([C:36]3[CH:35]=[CH:34][O:33][C:32]=3[CH:30]=[O:31])=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

7

Edukt 3

HCID 10796Cesium carbonateHCID 164141993-(Tetramethyl-1,3,2-dioxaborolan-2-yl)furan-2-carbaldehydeHCID 66685058Tert-butyl 6-(benzenesulfonylmethyl)-3-bromo-2-(2-hydroxy-acetylamino)benzoate2×

Produkt 1

HCID 86684734Tert-butyl 6-(benzenesulfonylmethyl)-3-(2-formylfuran-3-yl)-2-(2-hydroxyacetylamino)-benzoateAusbeute 99,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

A mixture of tert-butyl 6-(benzenesulfonylmethyl)-3-bromo-2-(2-hydroxyacetylamino)benzoate (Intermediate 36, 0.165 g), 2-formylfuran-3-boronic acid pinacol ester (0.091 g), 1,1′-bis(diphenylphosphino)ferrocene palladium dichloride DCM complex (0.028 g) and cesium carbonate (0.311 g) in THF (4.3 mL) and water (0.7 mL) were sealed, under nitrogen, in a microwave vial and heated in the microwave at 140° C. for 10 minutes. After cooling, the mixture was diluted with ethyl acetate and water and the organic layer was separated, washed with brine, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness to give tert-butyl 6-(benzenesulfonylmethyl)-3-(2-formylfuran-3-yl)-2-(2-hydroxyacetylamino)-benzoate (0.17 g).

Aufarbeitung

  1. customwere sealed, under nitrogen, in a microwave vial
  2. temperatureAfter cooling
  3. customthe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-f0db9ef8174347119d8834e12899a61b
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09266896B2

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