Trifluoroacetic acid → [5-(1-benzenesulfonyl-5-bromo-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-6-fluoro-pyridin-2-yl]-(5-fluoro-2-methoxy-pyridin-3-ylmethyl)-amine

HRID 510008Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 510008
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([Br:19])[CH:18]=[C:13]3[C:12]([CH2:20][C:21]3[CH:22]=[CH:23][C:24]([NH2:28])=[N:25][C:26]=3[F:27])=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:29][C:30]1[CH:31]=[C:32]([CH:38]=O)[C:33]([O:36][CH3:37])=[N:34][CH:35]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C(#N)C>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([Br:19])[CH:18]=[C:13]3[C:12]([CH2:20][C:21]3[CH:22]=[CH:23][C:24]([NH:28][CH2:38][C:32]4[C:33]([O:36][CH3:37])=[N:34][CH:35]=[C:30]([F:29])[CH:31]=4)=[N:25][C:26]=3[F:27])=[CH:11]2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

6

Edukt 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 226783235-Fluoro-2-methoxynicotinaldehydeHCID 67201069HCID 67201069, Verbindung

Produkt 1

HCID 67199844[5-(1-benzenesulfonyl-5-bromo-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-6-fluoro-pyridin-2-yl]-(5-fluoro-2-methoxy-pyridin-3-ylmethyl)-amineAusbeute 82,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To 5-(1-benzenesulfonyl-5-bromo-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-6-fluoro-pyridin-2-ylamine (167, 0.342 g, 0.741 mmol) in 10 mL of acetonitrile, 5-fluoro-2-methoxy-pyridine-3-carbaldehyde (37, 0.118 g, 0.763 mmol), triethylsilane (0.529 mL, 3.71 mmol) and trifluoroacetic acid (0.286 mL, 3.71 mmol) were added. The reaction was heated at 80° C. for 4 hours, then concentrated under vacuum and combined with aqueous potassium carbonate and extracted with ethyl acetate. The organic layer was washed with water and brine, then dried over magnesium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography eluting with ethyl acetate and hexane. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound as an off-white solid (168, 367 mg). MS (ESI) [M−H+]−=599.6 and 601.6.

Aufarbeitung

  1. concentrationconcentrated under vacuum
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under vacuum
  7. customThe resulting material was purified by silica gel column chromatography
  8. washeluting with ethyl acetate and hexane
  9. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-8990c30ad0e144f88a4bf99299cc12f0
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096593B2

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