Chlorosuccinimide → Ethyl (3-chloro-2H-pyrazolo[3,4-b]pyridin-2-yl)acetate

HRID 2112581Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2112581
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][N:6]1[CH:14]=[C:13]2[C:8]([N:9]=[CH:10][CH:11]=[CH:12]2)=[N:7]1)[CH3:2].C1C(=O)N([Cl:23])C(=O)C1>ClCCl>[CH2:1]([O:3][C:4](=[O:15])[CH2:5][N:6]1[C:14]([Cl:23])=[C:13]2[C:8]([N:9]=[CH:10][CH:11]=[CH:12]2)=[N:7]1)[CH3:2]

Komponenten

4

Edukt 2

HCID 31398ChlorosuccinimideHCID 57642783Ethyl (2H-pyrazolo[3,4-b]pyridin-2-yl)acetate

Produkt 1

HCID 57642771Ethyl (3-chloro-2H-pyrazolo[3,4-b]pyridin-2-yl)acetateAusbeute 97,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of pyrazolo[3,4-b]pyridin-2-yl-acetic acid ethyl ester 57 (40.2 mg, 0.2 mmol, 1 equiv) in 1 mL of dichloromethane was added NCS (32.7 mg, 1.2 mmol, 1.2 equiv). The resultant mixture was heated at 70° C. for 30 min., cooled to room temperature, and diluted with 100 mL of dichloromethane. The organic solution was washed with 50 mL of saturated sodium bicarbonate aqueous solution, and 50 mL of brine. The organic layer was separated and dried over sodium sulfate. Evaporation of solvent in vacuo gave 46.7 mg of (3-chloro-pyrazolo[3,4-b]pyridin-2-yl)-acetic acid ethyl ester as yellow solid.

Aufarbeitung

  1. washThe organic solution was washed with 50 mL of saturated sodium bicarbonate aqueous solution, and 50 mL of brine
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. customEvaporation of solvent in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-840c89aad18b4eb0a10ec74bd6769964
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07524845B2

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