Acetonitrile → HCID 58487345, Verbindung

HRID 1036094Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1036094
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[F:17])=[O:10])[CH:5]=[CH:4][C:3]=1Br.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[C:27](#[N:29])[CH3:28]>O1CCOCC1.O>[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[F:17])=[O:10])[CH:5]=[CH:4][C:3]=1[C:6]1[N:7]([CH3:2])[N:29]=[C:27]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:28]=1

Komponenten

6

Edukt 3

HCID 6342AcetonitrileHCID 62657Potassium Phosphate, TribasicHCID 58487036N-(6-amino-5-bromo(2-pyridyl))(2-fluorophenyl)carboxamide

Produkt 1

HCID 58487345HCID 58487345, VerbindungAusbeute 4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

A mixture of N-(6-amino-5-bromo(2-pyridyl))(2-fluorophenyl)carboxamide (61) (16 mg, 0.05 mmol), bis(ditertbutyl(4-dimethylaminophenyl)phosphine)dichloropalladium (II) (4 mg, 10% mol) and K3PO4 (11 mg, 0.05 mmol) in 0.5 ml ACN, 0.5 ml dioxane, 0.2 ml H2O was bubbled with argon before heated at 85° C. for 4 h. After cooling down to r.t., the reaction mixture was taken up in EA, washed with aq. NaHCO3 and brine. Org. phase was dried over Na2SO4, concentrated to dryness. Flash silica gel column purification (0-90% B, A: hexane; B: 50% EA in hexane) furnished 2.2 mg crude desired product as yellow solid which was re-purified on prep HPLC to give 0.8 mg N-[6-amino-5-(1-methyl-3-phenylpyrazol-5-yl)(2-pyridyl)](2-fluorophenyl)carboxamide (69) as off-white solid. (yield: 4%, purity>90%).

Aufarbeitung

  1. customwas bubbled with argon
  2. temperatureAfter cooling down to r.t.
  3. washwashed with aq. NaHCO3 and brine
  4. dry with materialphase was dried over Na2SO4
  5. concentrationconcentrated to dryness
  6. customFlash silica gel column purification (0-90% B
  7. customB: 50% EA in hexane) furnished 2.2 mg crude desired product as yellow solid which
  8. customwas re-purified on prep HPLC

Quellen und Nachweise

ORD-Eintrag
ord-a60c8cf1b6154e6299389adaaa2e4e22
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546403B2

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