Cyclohexylamine → N-Cyclohexyl-5-(methylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-amine

HRID 1506211Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1506211
Cl[C:2]1[C:7]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:6][N:5]=[C:4]2[N:12]([Si](C(C)C)(C(C)C)C(C)C)[CH:13]=[CH:14][C:3]=12.[CH:25]1([NH2:31])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.C(N(CC)C(C)C)(C)C>O>[CH:25]1([NH:31][C:2]2[C:3]3[CH:14]=[CH:13][NH:12][C:4]=3[N:5]=[CH:6][C:7]=2[S:8]([CH3:11])(=[O:9])=[O:10])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

Komponenten

5

Edukt 3

HCID 7965CyclohexylamineHCID 81531DiisopropylethylamineHCID 712584634-Chloro-5-(methylsulfonyl)-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine

Produkt 1

HCID 71258218N-Cyclohexyl-5-(methylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-amineAusbeute 15 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

4-Chloro-5-(methylsulfonyl)-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine (61 mg, 0.16 mmol) in cyclohexylamine (200 μL, 1.74 mmol) was stirred with N,N-diisopropylethylamine (40 μL, 0.23 mmol) at 120° C. for 30 minutes The reaction mixture was allowed to cool to room temperature and, after addition of water, extracted with chloroform, and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=20/1→5/1 (v/v)) to give the title compound as a colorless solid (7.0 mg, yield 15%).

Aufarbeitung

  1. extractionextracted with chloroform
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=20/1→5/1 (v/v))

Quellen und Nachweise

ORD-Eintrag
ord-e6cdc9bfba7f4063bc1439830d192745
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09216999B2

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