Ammonium Chloride → HCID 90311972, Verbindung

HRID 2170361Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2170361
[Br:1][C:2]1[C:3](/[CH:19]=[N:20]\[S@:21]([C:23]([CH3:26])([CH3:25])[CH3:24])=[O:22])=[N:4][CH:5]=[C:6]([N:8]2[C:16](=[O:17])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]2=[O:18])[CH:7]=1.[Br-].[F:28][C:29]1[CH:30]=[C:31]([CH:34]=[C:35]([F:37])[CH:36]=1)[CH2:32][Zn+].[Cl-].[NH4+]>C(Cl)Cl.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Cu+2]>[Br:1][C:2]1[C:3]([C@@H:19]([NH:20][S@:21]([C:23]([CH3:26])([CH3:25])[CH3:24])=[O:22])[CH2:32][C:31]2[CH:30]=[C:29]([F:28])[CH:36]=[C:35]([F:37])[CH:34]=2)=[N:4][CH:5]=[C:6]([N:8]2[C:9](=[O:18])[C:10]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:16]2=[O:17])[CH:7]=1

Komponenten

6

Edukt 3

HCID 25517Ammonium ChlorideHCID 90281260(NZ,S)-N-[[3-bromo-5-(1,3-dioxoisoindol-2-yl)-2-pyridinyl]methylidene]-2-methylpropane-2-sulfinamideHCID 178505922HCID 178505922, Verbindung

Produkt 1

HCID 90311972HCID 90311972, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2734996copper(II) trifluoromethanesulfonateKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (S,Z)—N-((3-bromo-5-(1,3-dioxoisoindolin-2-yl)pyridin-2-yl)methylene)-2-methylpropane-2-sulfinamide (30C, 3.7 G, 8.5 mmol) and Cu(OTf)2 (154 mg, 0.4 mmol) in methylene chloride (30 ml) at 0° C. was added (3,5-difluorobenzyl)zinc bromide (0.5 M in THF, 25.5 ml, 12.8 mmol) dropwise. The reaction stirred at room temperature for one hour. Ammonium chloride (aq, 100 ml) was added to the reaction and the mixture was extracted with methylene chloride (2×100 ml). The organic layer was dried over Na2SO4 filtered and concentrated (about 1:3 ratio of two diastereomers). The crude was purified by reverse phase HPLC eluting with acetonitrile and water (with 0.1% TFA) to afford the title compound as a single diastereomer. MS (m/z) 563.83 [M+H]+.

Aufarbeitung

  1. extractionthe mixture was extracted with methylene chloride (2×100 ml)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated (about 1:3 ratio of two diastereomers)
  5. customThe crude was purified by reverse phase HPLC
  6. washeluting with acetonitrile and water (with 0.1% TFA)

Quellen und Nachweise

ORD-Eintrag
ord-9c83ad2295c14a9a8284607b104fbda9
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09050344B2

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