N-methyl-2-pyrrolidone → 7-Bromo-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridin-4-ylamine

HRID 626736Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 626736
Br[C:2]1[C:7]2=[CH:8][N:9]([C:11]3[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:18])[N:10]=[C:6]2[C:5]([Br:19])=[CH:4][N:3]=1.C[N:21]1C(=O)CCC1>N>[Br:19][C:5]1[C:6]2[C:7](=[CH:8][N:9]([C:11]3[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:18])[N:10]=2)[C:2]([NH2:21])=[N:3][CH:4]=1

Komponenten

4

Edukt 2

HCID 13387N-methyl-2-pyrrolidoneHCID 866970594,7-Dibromo-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine

Produkt 1

HCID 696714737-Bromo-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridin-4-ylamineAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 222AmmoniaLösungsmittel

Versuchsvorschrift

A solution of 4,7-dibromo-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine (730 mg, 1.73 mmol) in NMP (6.5 mL) and 33% aqueous ammonia (3.5 mL) was sealed in a microwave vial and irradiated in a microwave reactor at 160° C. for 2 hours. 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 triturated with ether to afford the title compound as a beige solid (515 mg, 84% yield). LCMS (Method C): RT=2.00 min, m/z: 357 [M+H+].

Aufarbeitung

  1. customirradiated in a microwave reactor at 160° C. for 2 hours
  2. temperatureThe reaction mixture was cooled
  3. custompartitioned between ethyl acetate and water
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was triturated with ether

Quellen und Nachweise

ORD-Eintrag
ord-e94b00765d1b4ce58e573c40a1ce301f
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309240B2

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