Sodium Bicarbonate → 5-[2,6-Difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-{[6-(1H-pyrazol-5-yl)pyridazin-3-yl]amino}thiophene-3-carboxamide

HRID 386123Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 386123
Cl[C:2]1[N:7]=[N:6][C:5]([NH:8][C:9]2[S:10][C:11]([C:17]3[C:22]([F:23])=[CH:21][C:20]([C:24]([OH:27])([CH3:26])[CH3:25])=[CH:19][C:18]=3[F:28])=[CH:12][C:13]=2[C:14]([NH2:16])=[O:15])=[CH:4][CH:3]=1.[NH:29]1[CH:33]=[CH:32][C:31](B(O)O)=[N:30]1.C(=O)(O)[O-].[Na+]>C1COCC1>[F:28][C:18]1[CH:19]=[C:20]([C:24]([OH:27])([CH3:26])[CH3:25])[CH:21]=[C:22]([F:23])[C:17]=1[C:11]1[S:10][C:9]([NH:8][C:5]2[N:6]=[N:7][C:2]([C:31]3[NH:30][N:29]=[CH:33][CH:32]=3)=[CH:3][CH:4]=2)=[C:13]([C:14]([NH2:16])=[O:15])[CH:12]=1

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 595261282-[(6-Chloropyridazin-3-yl)amino]-5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]thiophene-3-carboxamideHCID 178514837HCID 178514837, Verbindung

Produkt 1

HCID 595262175-[2,6-Difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-{[6-(1H-pyrazol-5-yl)pyridazin-3-yl]amino}thiophene-3-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 2-[(6-chloropyridazin-3-yl)amino]-5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]thiophene-3-carboxamide (64 mg, 0.15 mmol) in THF (3 ml), was added 1H-pyrazol-3-yl boronic acid (34 mg, 0.30 mmol), and sodium bicarbonate (0.38 ml, 0.75 mmol, 2 M). Palladium tetrakis triphenylphosphine (35 mg, 0.03 mmol) was added last and the vial was purged with nitrogen for 5 minutes. The crude product was washed with 3:1 chloroform:isopropanol and water. The resulting organic layer was dried over magnesium sulfate and concentrated under reduced pressure. Purification by column chromatography yielded the title compound.

Aufarbeitung

  1. customthe vial was purged with nitrogen for 5 minutes
  2. washThe crude product was washed with 3:1 chloroform
  3. dry with materialThe resulting organic layer was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customPurification by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-16802d7c304247d2b6e045e626af355d
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367706B2

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