Cesium carbonate → HCID 67271616, Verbindung

HRID 1696474Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1696474
Cl.Br[C:3]1[CH:4]=[C:5]([N:9]2[C:13]([NH2:14])=[CH:12][C:11]([C:15]([CH3:18])([CH3:17])[CH3:16])=[N:10]2)[CH:6]=[CH:7][CH:8]=1.CC1(C)C(C)(C)OB([C:27]2[CH:28]=[N:29][N:30](C(OC(C)(C)C)=O)[CH:31]=2)O1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[NH:29]1[CH:28]=[C:27]([C:3]2[CH:4]=[C:5]([N:9]3[C:13]([NH2:14])=[CH:12][C:11]([C:15]([CH3:18])([CH3:17])[CH3:16])=[N:10]3)[CH:6]=[CH:7][CH:8]=2)[CH:31]=[N:30]1

Komponenten

7

Edukt 3

HCID 10796Cesium carbonateHCID 16217654tert-butyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylateHCID 534073321-(3-Bromophenyl)-3-tert-butyl-1H-pyrazol-5-amine--hydrogen chloride (1/1)

Produkt 1

HCID 67271616HCID 67271616, VerbindungAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 962WaterLösungsmittel2×HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A solution of 1-(3-bromophenyl)-3-t-butyl-1H-pyrazol-5-amine hydrochloride (0.253 g, 0.77 mmol, available from Example 54), t-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate (0.28 g, 0.95 mmol, commercially available) and Cs2CO3 (1.0 g, 3.1 mmol) in DMF (5 mL) and H2O (2 mL) was placed under Ar for 15 min. Palladium tetrakis(triphenylphosphine) was added and the reaction mixture was heated at 80° C. overnight. The reaction mixture was poured into H2O (20 mL) and extracted with EtOAc (2×30 mL). The extracts were washed with H2O (10 mL) and brine (10 mL), dried (Na2SO4) concentrated and purified via column chromatography to yield 1-(3-(1H-pyrazol-4-yl)phenyl)-3-t-butyl-1H-pyrazol-5-amine (163 mg, 76% yield). MS (ESI) m/z: 282.3 (M+H+).

Aufarbeitung

  1. extractionextracted with EtOAc (2×30 mL)
  2. washThe extracts were washed with H2O (10 mL) and brine (10 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. custompurified via column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-4babff8357594ae2a7b19f34bf0b8bd3
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163756B2

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