Sodium hydride → 6-[2-(2,6-Dichlorophenyl)-2H-pyrazolo[4,3-c]pyridin-4-ylamino]nicotinonitrile

HRID 626661

Reaktionsgleichung

Reaktionsgleichung von HRID 626661
[H-].[Na+].[NH2:3][C:4]1[N:9]=[CH:8][C:7]([C:10]#[N:11])=[CH:6][CH:5]=1.Cl[C:13]1[C:18]2=[CH:19][N:20]([C:22]3[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][C:23]=3[Cl:29])[N:21]=[C:17]2[CH:16]=[CH:15][N:14]=1>CN(C=O)C>[Cl:29][C:23]1[CH:24]=[CH:25][CH:26]=[C:27]([Cl:28])[C:22]=1[N:20]1[CH:19]=[C:18]2[C:13]([NH:3][C:4]3[CH:5]=[CH:6][C:7]([C:10]#[N:11])=[CH:8][N:9]=3)=[N:14][CH:15]=[CH:16][C:17]2=[N:21]1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 8182602-Amino-5-cyanopyridineHCID 866970364-chloro-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine

Produkt 1

HCID 696717086-[2-(2,6-Dichlorophenyl)-2H-pyrazolo[4,3-c]pyridin-4-ylamino]nicotinonitrileAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Sodium hydride (12 mg, 0.30 mmol) was added to a solution of 6-amino-3-pyridinecarbonitrile (36 mg, 0.30 mmol) in DMF (2 mL) and the resultant mixture was stirred for 5 minutes before 4-chloro-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine (80 mg, 0.27 mmol) was added. The reaction vial was sealed, purged with nitrogen and irradiated in a microwave at 150° C. for 10 minutes. The reaction mixture was cooled and partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (40% ethyl acetate in cyclohexane) to afford the title compound as a yellow solid (53 mg, 52% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.57 (d, J=0.9 Hz, 1H), 8.98 (dd, J=2.3, 0.8 Hz, 1H), 8.47 (dd, J=8.7, 2.3 Hz, 1H), 8.04 (d, J=7.3 Hz, 1H), 7.89-7.83 (m, 2H), 7.77 (dd, J=9.1, 7.2 Hz, 1H), 7.65-7.61 (m, 2H). LCMS (Method B): RT=3.05 min, m/z: 381 [M+H+].

Aufarbeitung

  1. additionwas added
  2. customThe reaction
  3. customvial was sealed
  4. custompurged with nitrogen
  5. customirradiated in a microwave at 150° C. for 10 minutes
  6. temperatureThe reaction mixture was cooled
  7. custompartitioned between ethyl acetate and water
  8. washThe organic layer was washed with brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by silica gel flash chromatography (40% ethyl acetate in cyclohexane)

Quellen und Nachweise

ORD-Eintrag
ord-6ff535f1486242bdb4edf8bf6b0469ec
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309240B2

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