Cesium carbonate → HCID 71144315, Verbindung

HRID 2370801Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2370801
[F:1][C:2]1[C:3]([C@H:8]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=2)[NH:9][C:10](=[O:18])[C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][N:12]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.C([O:33][C:34](=[O:37])[CH2:35]Br)(C)(C)C.C(=O)([O-])[O-].[Cs+].[Cs+]>C(Cl)Cl.CN(C=O)C>[F:1][C:2]1[C:3]([C@@H:8]([NH:9][C:10]([C:11]2[N:12]=[CH:13][C:14]([O:17][CH2:35][C:34]([OH:37])=[O:33])=[CH:15][CH:16]=2)=[O:18])[C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:26])[F:27])=[CH:21][CH:20]=2)=[N:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 79177tert-Butyl bromoacetateHCID 71144553HCID 71144553, Verbindung

Produkt 1

HCID 71144315HCID 71144315, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (S)—N-((3-fluoropyridin-2-yl)(4-(trifluoromethyl)phenyl)-methyl)-5-hydroxypicolinamide (Example 173) (0.145 g, 0.371 mmol) in DCM (2 mL) and DMF (0.2 mL) were added bromoacetic acid t-butyl ester (0.072 mL, 0.445 mmol) and cesium carbonate (0.241 g, 0.741 mmol). The resulting mixture was then stirred at rt for 2 h. Then, the mixture was filtered and the solid was washed with DCM (1×1 mL) and MeOH (1×1 mL). The combined filtrates were concentrated and dried to give the desired product, which was used without further purification in the next step.

Aufarbeitung

  1. filtrationThen, the mixture was filtered
  2. washthe solid was washed with DCM (1×1 mL) and MeOH (1×1 mL)
  3. concentrationThe combined filtrates were concentrated
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-ea6a536416474cda8ad19b81f7252086
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08710043B2

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