2,2'-Bipyridine → 2-[5-(2-Aminomethyl-4-fluorophenoxy)-indazol-1-yl]-N,N-dimethylacetamide

HRID 909221Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 909221
[C:1]([C:3]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:4]=1[O:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:15][C:16]([N:18]([CH3:20])[CH3:19])=[O:17])[N:10]=[CH:9]2)#[N:2].N1C=CC=CC=1C1C=CC=CN=1.[BH4-].[Na+]>CCO>[NH2:2][CH2:1][C:3]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:4]=1[O:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:15][C:16]([N:18]([CH3:20])[CH3:19])=[O:17])[N:10]=[CH:9]2

Komponenten

5

Edukt 3

HCID 14742,2'-Bipyridine2×HCID 4311764Sodium borohydride2×HCID 674094872-[5-(2-Cyano-4-fluorophenoxy)-indazol-1-yl]-N,N-dimethylacetamide

Produkt 1

HCID 674102372-[5-(2-Aminomethyl-4-fluorophenoxy)-indazol-1-yl]-N,N-dimethylacetamideAusbeute 11 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 2-[5-(2-cyano-4-fluorophenoxy)-indazol-1-yl]-N,N-dimethylacetamide (0.090 g, 0.266 mmol) in EtOH (0.5 mL) was added CoBr2 (27 μL, 0.005 mmol) followed by [2,2′]bipyridinyl (81 μL, 0.015 mmol). NaBH4 (0.030 g, 0.798 mmol) was added to the mixture and it was stirred at room temperature for 18 hours. The mixture was treated with another portion each of CoBr2, [2,2′]bipyridinyl, and NaBH4 and stirred for another 18 hours. The mixture was quenched with MeOH, followed by acetic acid and then concentrated under reduced pressure. The white residue was partitioned between saturated NaHCO3 and ethyl acetate. The organic layer was filtered and concentrated under reduced pressure to afford 10 mg of white solid (11% yield).

Aufarbeitung

  1. stirringstirred for another 18 hours
  2. customThe mixture was quenched with MeOH
  3. concentrationconcentrated under reduced pressure
  4. customThe white residue was partitioned between saturated NaHCO3 and ethyl acetate
  5. filtrationThe organic layer was filtered
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ddb2b7bf2d0946c9ad8273ba7a2a6d96
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08017641B2

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