Dimethylformamide → 3-(1,4,Diazabicyclo[3.2.2]non-4-ylcarbonyl)-1h-pyrazolo[3,4-c]pyridine

HRID 37815

Reaktionsgleichung

Reaktionsgleichung von HRID 37815
Br[C:2]1[C:10]2[C:5](=[CH:6][N:7]=[CH:8][CH:9]=2)[NH:4][N:3]=1.[N:11]12[CH2:19][CH2:18][CH:15]([CH2:16][CH2:17]1)[NH:14][CH2:13][CH2:12]2.C(N(CC)CC)C.CN(C)[CH:29]=[O:30]>C1(P([Pd](P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(Cl)Cl)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[N:11]12[CH2:19][CH2:18][CH:15]([CH2:16][CH2:17]1)[N:14]([C:29]([C:2]1[C:10]3[C:5](=[CH:6][N:7]=[CH:8][CH:9]=3)[NH:4][N:3]=1)=[O:30])[CH2:13][CH2:12]2

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 3984071,4-Diazabicyclo(3.2.2)nonaneHCID 178419486HCID 178419486, Verbindung

Produkt 1

HCID 689680133-(1,4,Diazabicyclo[3.2.2]non-4-ylcarbonyl)-1h-pyrazolo[3,4-c]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 178479802HCID 178479802, VerbindungKatalysator

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

1 g (5 mmol) of 3-bromo-1H-pyrazolo[3,4-c]-pyridine, 0.53 g (0.75 mmol) of bis(triphenylphosphino)dichloropalladium, 1.9 g (15.1 mmol) of 1,4-diazabicyclo[3.2.2]nonane and 3.5 ml (25 mmol) of triethylamine dissolved in 15 ml of N,N-dimethylformamide are successively introduced into a 50 ml reactor. The mixture is then purged with carbon monoxide and heated at 110° C. for 20 hours. The reaction medium is poured into 100 ml of water and the aqueous phase is extracted with chloroform. After drying the organic phases, they are dried, filtered and concentrated under reduced pressure. The residue is purified by chromatography on a column of silica gel, eluting with a mixture of chloroform, methanol and aqueous ammonia in 90/10/1 proportions.

Aufarbeitung

  1. additionare successively introduced into a 50 ml reactor
  2. customThe mixture is then purged with carbon monoxide
  3. additionThe reaction medium is poured into 100 ml of water
  4. extractionthe aqueous phase is extracted with chloroform
  5. customAfter drying the organic phases, they
  6. customare dried
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue is purified by chromatography on a column of silica gel
  10. washeluting with a mixture of chloroform, methanol and aqueous ammonia in 90/10/1 proportions

Quellen und Nachweise

ORD-Eintrag
ord-814e87e08ebe42e0a69e2333a633230c
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524706B2

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