Trifluoroacetic acid → 6-fluoro-5-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyridin-2-ylamine

HRID 509982Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 509982
C(OC(=O)[N:7]([C:17]1[CH:22]=[CH:21][C:20]([CH:23](O)[C:24]2[C:32]3[C:27](=[N:28][CH:29]=[C:30]([CH3:33])[CH:31]=3)[N:26]([Si](C(C)C)(C(C)C)C(C)C)[CH:25]=2)=[C:19]([F:45])[N:18]=1)CC1C=CC(OC)=CC=1)(C)(C)C.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C(#N)C>[F:45][C:19]1[N:18]=[C:17]([NH2:7])[CH:22]=[CH:21][C:20]=1[CH2:23][C:24]1[C:32]2[C:27](=[N:28][CH:29]=[C:30]([CH3:33])[CH:31]=2)[NH:26][CH:25]=1

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 58258936{6-fluoro-5-[hydroxy-(5-methyl-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-methyl]-pyridin-2-yl}-(4-methoxy-benzyl)-carbamic acid tert-butyl ester

Produkt 1

HCID 582592126-fluoro-5-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyridin-2-ylamineAusbeute 62,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To {6-fluoro-5-[hydroxy-(5-methyl-1-triisopropylsilanyl-1H-pyrrol [2,3-b]pyridin-3-yl)-methyl]-pyridin-2-yl}-(4-methoxy-benzyl)-carbamic acid tert-butyl ester (136, 21 g, 32.4 mmol) in 500 mL of acetonitrile, triethylsilane (51.7 mL, 324 mmol) and trifluoroacetic acid (24.93 mL, 324 mmol) were added. The reaction was stirred at 50° C. for several hours, solvents removed under vacuum, and the residue taken up in 250 mL of dichloromethane and 250 mL of trifluoroacetic acid was added. The mixture was stirred at reflux for several hours, then concentrated under vacuum. The residue was taken up in ethyl acetate and poured into aqueous potassium carbonate. The organic layer was separated, concentrated under vacuum and purified by silica gel column chromatography, eluting with 0-5% methanol in dichloromethane. Appropriate fractions were combined and the solvents removed under vacuum to provide the desired compound (137, 5.2 g, 20.29 mmol, 62.7% yield).

Aufarbeitung

  1. customsolvents removed under vacuum
  2. addition250 mL of trifluoroacetic acid was added
  3. stirringThe mixture was stirred
  4. temperatureat reflux for several hours
  5. concentrationconcentrated under vacuum
  6. additionpoured into aqueous potassium carbonate
  7. customThe organic layer was separated
  8. concentrationconcentrated under vacuum
  9. custompurified by silica gel column chromatography
  10. washeluting with 0-5% methanol in dichloromethane
  11. customthe solvents removed under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-f1baa994e58d47779ea7e2c392ed463e
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096593B2

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