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Cesium carbonate → 6-(1-tert-butyl-1H-pyrazol-4-yl)-3-methyl-4-(methylthio)-3H-imidazo[4,5-c]pyridine

HRID 2209011
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2209011
Cl[C:2]1[N:7]=[C:6]([S:8][CH3:9])[C:5]2[N:10]([CH3:13])[CH:11]=[N:12][C:4]=2[CH:3]=1.ClC1N=C(SC)C2N=CN(C)C=2C=1.[C:27]([N:31]1[CH:35]=[C:34](C2OC(C)(C)C(C)(C)O2)[CH:33]=[N:32]1)([CH3:30])([CH3:29])[CH3:28].C([O-])([O-])=O.[Cs+].[Cs+]>C(C1C=CC=C(C(C)C)C=1N1C=CN(C2C(C(C)C)=CC=CC=2C(C)C)C1=[Pd-3](Cl)(Cl)C1C(Cl)=CC=CN=1)(C)C.O.COCCOC>[C:27]([N:31]1[CH:35]=[C:34]([C:2]2[N:7]=[C:6]([S:8][CH3:9])[C:5]3[N:10]([CH3:13])[CH:11]=[N:12][C:4]=3[CH:3]=2)[CH:33]=[N:32]1)([CH3:30])([CH3:29])[CH3:28]
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Komponenten

8

Edukt 4

HCID 10796Cesium carbonateHCID 1178431521-tert-butyl-4-(4,4,5,5-tetramethyl-1,3-dioxolan-2-yl)-1H-pyrazoleHCID 1178433356-chloro-1-methyl-4-(methylthio)-1H-imidazo[4,5-c]pyridineHCID 1178434146-chloro-3-methyl-4-(methylthio)-3H-imidazo[4,5-c]pyridine

Produkt 1

HCID 1178438386-(1-tert-butyl-1H-pyrazol-4-yl)-3-methyl-4-(methylthio)-3H-imidazo[4,5-c]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178439029HCID 178439029, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

To a mixture of 6-chloro-3-methyl-4-(methylthio)-3H-imidazo[4,5-c]pyridine 2.02 and 6-chloro-1-methyl-4-(methylthio)-1H-imidazo[4,5-c]pyridine 2.03 (prepared as previously described, ˜1:2 mixture of regioisomers, 1.25 g, 5.85 mmol),1-tert-butyl-4-(4,4,5,5-tetramethyl-1,3-dioxolan-2-yl)-1H-pyrazole (2.20 g, 8.78 mmol), and Cs2CO3 (5.72 g, 17.6 mmol) was added DME (20 mL) and water (10 mL) and the solution was degassed for 10 min. [1,3-Bis(2,6-Diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) dichloride (397 mg, 0.585 mmol) was added and the reaction was heated to 100 deg C. for 1 hour. Upon cooling, the aqueous layer was removed, EtOAc and water were added, and the layers separated. The organic layer was dried (MgSO4), filtered and concentrated. The residue was purified by flash chromatography (EtOAc 0-->5% MeOH gradient) to afford 6-(1-tert-butyl-1H-pyrazol-4-yl)-3-methyl-4-(methylthio)-3H-imidazo[4,5-c]pyridine 2.39 and 6-(1-tert-butyl-1H-pyrazol-4-yl)-3-methyl-4-(methylthio)-3H-imidazo[4,5-c]pyridine 2.40, which were isolated as a mixture and carried directly into the next step.

Aufarbeitung

  1. customprepared
  2. additionwas added
  3. temperaturethe reaction was heated to 100 deg C
  4. temperatureUpon cooling
  5. customthe aqueous layer was removed
  6. additionEtOAc and water were added
  7. customthe layers separated
  8. dry with materialThe organic layer was dried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe residue was purified by flash chromatography (EtOAc 0-->5% MeOH gradient)

Quellen und Nachweise

ORD-Eintrag
ord-66678d11df444beb935874d4c5aa8a06
Quelldatensatz
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09376441B2

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