Dimethylformamide → HCID 71253450, Verbindung

HRID 1775088Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1775088
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]3[C:15]([Sn](C)(C)C)=[N:14][N:13]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[C:10]3=[CH:11][N:12]=2)[CH:2]=1.[Br:28][C:29]1[C:30]([F:36])=[N:31][C:32](I)=[CH:33][CH:34]=1.CN(C)C=O.[F-].[Cs+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[Br:28][C:29]1[CH:34]=[CH:33][C:32]([C:15]2[C:9]3[C:10](=[CH:11][N:12]=[C:7]([C:3]4[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=4)[CH:8]=3)[N:13]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[N:14]=2)=[N:31][C:30]=1[F:36]

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 25953Cesium fluorideHCID 71253848HCID 71253848, VerbindungHCID 717430873-Bromo-2-fluoro-6-iodopyridine

Produkt 1

HCID 71253450HCID 71253450, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418397HCID 178418397, VerbindungKatalysator

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To an argon protected mixture of 5-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-3-(trimethylstannyl)-1H-pyrazolo[3,4-c]pyridine (239 mg, 0.489 mmol) and 3-bromo-2-fluoro-6-iodopyridine (162.3 mg, 0.538 mmol) in N,N-Dimethylformamide (5 mL, 60 mmol) was added Cesium fluoride (148 mg, 0.98 mmol). Tetrakis(triphenylphosphine)palladium(0) (56.482 mg, 0.048878 mmol) and Copper(I) iodide (18.618 mg, 0.097757 mmol) were then added and the resulting mixture was stirred at 40° C. for 2 hours. The mixture was cooled to room temperature, filtered through Celite®. The filter cake was washed with EtOAc. The organic layer was washed with brine, dried with MgSO4, and then concentrated. The residue was purified on silica eluted with 0 to 100% EtOAc in Heptane to afford 3-(5-bromo-6-fluoropyridin-2-yl)-5-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridine as a light yellow oil, which solidified upon standing (208.1 mg, 85%).

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered through Celite®
  3. washThe filter cake was washed with EtOAc
  4. washThe organic layer was washed with brine
  5. dry with materialdried with MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified on silica
  8. washeluted with 0 to 100% EtOAc in Heptane

Quellen und Nachweise

ORD-Eintrag
ord-ddf5a3ecb412466a84c8d76e83ff0d27
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09260425B2

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