Nicotinic Acid → N-(5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)nicotinamide

HRID 79614

Reaktionsgleichung

Reaktionsgleichung von HRID 79614
[Br:1][C:2]1[C:3]([F:12])=[C:4]2[C:10]([NH2:11])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[C:13](O)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[N:16][CH:15]=1.C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1.C(N(CC)CC)C.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.[Li+].[OH-]>[Br:1][C:2]1[C:3]([F:12])=[C:4]2[C:10]([NH:11][C:13](=[O:20])[C:14]3[CH:19]=[CH:18][CH:17]=[N:16][CH:15]=3)=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Komponenten

8

Edukt 5

HCID 938Nicotinic AcidHCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 602052765-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine

Produkt 1

HCID 60205277N-(5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)nicotinamideAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3939Lithium HydroxideLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

5-Bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine (0.044 g, 0.19 mmol), nicotinic acid (0.0283 g, 0.230 mmol), and BOP-Cl (0.0584 g, 0.230 mmol) were placed in DMF (3 mL) at room temperature. Triethylamine (0.133 mL, 0.956 mmol) was then added, and the reaction was stirred for 1 hour at room temperature. The reaction was then diluted with 3M LiOH (aq., 0.5 mL) and stirred for 10 minutes. The reaction was then poured into saturated Na2CO3, extracted into DCM, and the organic fractions were combined, dried, filtered and concentrated to give a crude residue. The crude residue was triturated with 1:2 MeOH/DCM to give N-(5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)nicotinamide (0.035 g, 54.6% yield) as a solid.

Aufarbeitung

  1. stirringstirred for 10 minutes
  2. extractionextracted into DCM
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a crude residue
  7. customThe crude residue was triturated with 1:2 MeOH/DCM

Quellen und Nachweise

ORD-Eintrag
ord-5061f5e55d624c41b472ecbf109cce71
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841304B2

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