5-Bromo-N-methoxy-N-methylpyridine-3-carboxamide → (5-bromopyridin-3-yl)[1-(2-{[tert-butyl(dimethyl)silyl]oxy}-1,1-dimethylethyl)-1H-pyrrolo[3,2-c]pyridin-3-yl]methanone

HRID 1753053Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1753053
[Si:1]([O:8][CH2:9][C:10]([N:13]1[C:21]2[CH:20]=[CH:19][N:18]=[CH:17][C:16]=2[C:15](I)=[CH:14]1)([CH3:12])[CH3:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C([Mg]Cl)(C)C.[Br:28][C:29]1[CH:30]=[N:31][CH:32]=[C:33]([CH:40]=1)[C:34](N(OC)C)=[O:35]>C1COCC1>[Br:28][C:29]1[CH:40]=[C:33]([C:34]([C:15]2[C:16]3[CH:17]=[N:18][CH:19]=[CH:20][C:21]=3[N:13]([C:10]([CH3:12])([CH3:11])[CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH:14]=2)=[O:35])[CH:32]=[N:31][CH:30]=1

Komponenten

5

Edukt 3

HCID 184722695-Bromo-N-methoxy-N-methylpyridine-3-carboxamideHCID 900934361-(2-{[tert-butyl(dimethyl)silyl]oxy}-1,1-dimethylethyl)-3-iodo-1H-pyrrolo[3,2-c]pyridineHCID 178418918HCID 178418918, Verbindung

Produkt 1

HCID 90092809(5-bromopyridin-3-yl)[1-(2-{[tert-butyl(dimethyl)silyl]oxy}-1,1-dimethylethyl)-1H-pyrrolo[3,2-c]pyridin-3-yl]methanoneAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Reaktionsbedingungen

Temperatur
-5 °C

Versuchsvorschrift

1-(2-{[tert-butyl(dimethyl)silyl]oxy}-1,1-dimethylethyl)-3-iodo-1H-pyrrolo[3,2-c]pyridine (Preparation 65, 1.81 g, 4.20 mmol) was dissolved in THF (25 mL) and the solution was degassed and cooled to −5° C. 2M iPrMgCl in THF (2.52 mL, 5.05 mmol) was added dropwise and the reaction stirred at this temperature for 45 minutes. A solution of 5-bromo-N-methoxy-N-methylnicotinamide (1.24 g, 5.05 mmol) in THF (3 mL) was added dropwise and the reaction warmed to room temperature for 4.5 hours. The reaction was partitioned between saturated aqueous ammonium chloride solution (20 mL) and EtOAc (30 mL). The organic layer was collected, dried and concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with 100% DCM to 50:50 DCM:EtOAc to afford the title compound as a colourless oil (1.05 g, 62%).

Aufarbeitung

  1. customthe solution was degassed
  2. temperaturethe reaction warmed to room temperature for 4.5 hours
  3. customThe reaction was partitioned between saturated aqueous ammonium chloride solution (20 mL) and EtOAc (30 mL)
  4. customThe organic layer was collected
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified
  8. washeluting with 100% DCM to 50:50 DCM

Quellen und Nachweise

ORD-Eintrag
ord-71d1cc2d7c8448d9bcdf2ce8d3c29eb9
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09163021B2

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