Potassium Carbonate → Ethyl 4-ethoxy-1-pent-3-ynyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate

HRID 1252699Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1252699
[CH2:1]([O:3][C:4]([C:6]1[C:7]([O:15][CH2:16][CH3:17])=[C:8]2[CH:14]=[N:13][NH:12][C:9]2=[N:10][CH:11]=1)=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][CH2:26][C:27]#[C:28][CH3:29]>CN(C=O)C>[CH2:16]([O:15][C:7]1[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:11][N:10]=[C:9]2[N:12]([CH2:29][CH2:28][C:27]#[C:26][CH3:25])[N:13]=[CH:14][C:8]=12)[CH3:17]

Komponenten

5

Edukt 3

HCID 11430Potassium Carbonate2×HCID 124762055-Bromopent-2-yne2×HCID 14590535CID 14590535

Produkt 1

HCID 14590534Ethyl 4-ethoxy-1-pent-3-ynyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of the ethyl-4-ethoxy-1H-pyrazolo[3,4-b]pyridine-5-carboxylate of Example 19c (8.13 g.), pulverized anhydrous potassium carbonate (14.3 g.) and 1-bromo-3-pentyne (10.7 g.) in dry DMF (58 ml.) was stirred at 55°-60° for 4.5 hours. Additional quantities of 1-bromo-3-pentyne (5.3 g.) and potassium carbonate (14.3 g.) were added after 1 hour. The mixture was cooled and filtered and the filtrate evaporated at 45°-50°. The residue was diluted with water and extracted with ether and EtOAc. The combined extracts were washed with water, dried (MgSO4) and evaporated. The residue was purified by chromatography on silica gel using EtOAc/hexane 1:1 v/v as eluant to give the title compound, m.p. 93°-95°, after recrystallization from toluene.

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. customthe filtrate evaporated at 45°-50°
  4. additionThe residue was diluted with water
  5. extractionextracted with ether and EtOAc
  6. washThe combined extracts were washed with water
  7. dry with materialdried (MgSO4)
  8. customevaporated
  9. customThe residue was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-1f7c08d7c64d4cbfa576e85975811ba1
Quelldatensatz
uspto-grants-1988_05
Patentnummer
US04745121

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