18-Crown-6 → (E)-tert-butyl 2-(5-(3-(3,5-dichloro-4-fluorophenyl)-4,4,4-trifluorobut-1-enyl)-1H-indol-1-yl)-2-oxoethylcarbamate

HRID 1503705Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1503705
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]([C:22]([F:25])([F:24])[F:23])/[CH:11]=[CH:12]/[C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[NH:18][CH:17]=[CH:16]3)[CH:5]=[C:6]([Cl:9])[C:7]=1[F:8].[C:26]([O:30][C:31]([NH:33][CH2:34][C:35](OC1C=CC([N+]([O-])=O)=CC=1)=[O:36])=[O:32])([CH3:29])([CH3:28])[CH3:27].[F-].[K+].C1OCCOCCOCCOCCOCCOC1.CCN(C(C)C)C(C)C>C(#N)C.C(Cl)Cl>[Cl:9][C:6]1[CH:5]=[C:4]([CH:10]([C:22]([F:24])([F:23])[F:25])/[CH:11]=[CH:12]/[C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[N:18]([C:35](=[O:36])[CH2:34][NH:33][C:31](=[O:32])[O:30][C:26]([CH3:27])([CH3:28])[CH3:29])[CH:17]=[CH:16]3)[CH:3]=[C:2]([Cl:1])[C:7]=1[F:8]

Komponenten

8

Edukt 5

HCID 2855718-Crown-6HCID 77217Boc-Gly-ONpHCID 81531DiisopropylethylamineHCID 522689Potassium FluorideHCID 86675169(E)-5-(3-(3,5-dichloro-4-fluorophenyl)-4,4,4-trifluorobut-1-en-1-yl)-1H-indole

Produkt 1

HCID 86675171(E)-tert-butyl 2-(5-(3-(3,5-dichloro-4-fluorophenyl)-4,4,4-trifluorobut-1-enyl)-1H-indol-1-yl)-2-oxoethylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of (E)-5-(3-(3,5-dichloro-4-fluorophenyl)-4,4,4-trifluorobut-1-enyl)-1H-indole (0.1 g, 0.258 mmol) in acetonitrile (5.0 mL) was added 4-nitrophenyl 2-(tert-butoxycarbonylamino)acetate (0.114 g, 0.387 mmol), potassium fluoride (0.03 g, 0.516 mmol), 18-crown-6-ether (0.075 g, 0.283 mmol) and DIEA (0.0332 g, 0.258 mmol) and the reaction was stirred at RT for 16 h. The reaction mixture was concentrated to obtain a residue which was diluted with DCM and washed with water and brine solution. The separated DCM layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford the crude title compound as a light brown gummy material which was used in the next step without further purification (0.1 g): ESIMS m/z 545.23 ([M+H]+).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. customto obtain a residue which
  3. washwashed with water and brine solution
  4. dry with materialThe separated DCM layer was dried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-368eb2b852674a5ea7ff0d120ce86ef6
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09212164B2

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