Dimethylacetamide → 5-(1-Benzyl-1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine

HRID 1054400

Reaktionsgleichung

Reaktionsgleichung von HRID 1054400
Br[C:2]1[N:7]2[N:8]=[C:9]([NH2:11])[N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.[CH2:12]([N:19]1[CH:23]=[C:22](B(O)O)[CH:21]=[N:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CC(N(C)C)=O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH2:12]([N:19]1[CH:23]=[C:22]([C:2]2[N:7]3[N:8]=[C:9]([NH2:11])[N:10]=[C:6]3[CH:5]=[CH:4][CH:3]=2)[CH:21]=[N:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

7

Edukt 4

HCID 31374DimethylacetamideHCID 62657Potassium Phosphate, TribasicHCID 33528811-Benzyl-1H-pyrazole-4-boronic acidHCID 252159395-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine

Produkt 1

HCID 445556945-(1-Benzyl-1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A vial was charged with 5-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (2.00 g, 9.39 mmol), 1-benzylpyrazole-4-boronic acid, pinacol ester (3.20 g, 11.3 mmol), potassium phosphate (4.00 g, 18.8 mmol) and tetrakis(triphenylphosphine)palladium (1.10 g, 0.94 mmol). Dimethylacetamide (24 ml) and water (8 ml) were added and the reaction mixture was heated under microwave irradiation to 150° C. for 10 min. The mixture was partitioned between ethyl acetate and water, and the aqueous phase extracted with ethyl acetate. The combined organic phases were washed several times with water, once with brine, dried over magnesium sulfate and concentrated in vacuo. Trituration in the minimum amount of dichloromethane and diethyl ether afforded an orange solid which required no further purification. Yield: 1.82 g, 67%; LCMS method: 2, RT: 2.37 min, MI: 291 [M+1].

Aufarbeitung

  1. customThe mixture was partitioned between ethyl acetate and water
  2. extractionthe aqueous phase extracted with ethyl acetate
  3. washThe combined organic phases were washed several times with water
  4. dry with materialonce with brine, dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customTrituration in the minimum amount of dichloromethane and diethyl ether afforded an orange solid which
  7. customno further purification

Quellen und Nachweise

ORD-Eintrag
ord-afd573a4849c49319f85e42ddb680282
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394301B2

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