Potassium Carbonate → 4-(1-Ethyl-3-(4-nitrophenyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine

HRID 28917Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 28917
[CH2:1]([N:3]1[CH:7]=[C:6](B2OC(C)(C)C(C)(C)O2)[C:5]([C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)=[N:4]1)[CH3:2].Br[C:27]1[CH:32]=[CH:31][N:30]=[C:29]2[NH:33][CH:34]=[CH:35][C:28]=12.C(=O)([O-])[O-].[K+].[K+]>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.O1CCOCC1>[CH2:1]([N:3]1[CH:7]=[C:6]([C:27]2[CH:32]=[CH:31][N:30]=[C:29]3[NH:33][CH:34]=[CH:35][C:28]=23)[C:5]([C:17]2[CH:18]=[CH:19][C:20]([N+:23]([O-:25])=[O:24])=[CH:21][CH:22]=2)=[N:4]1)[CH3:2]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 222736434-Bromo-1H-pyrrolo[2,3-b]pyridineHCID 689953481-ethyl-3-(4-nitrophenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Produkt 1

HCID 689951784-(1-Ethyl-3-(4-nitrophenyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridineAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of 1-ethyl-3-(4-nitrophenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (7.5 mmol), 4-bromo-1H-pyrrolo[2,3-b]pyridine (Ref Org. Lett. 5(26), 5023-5024, 2003) (6.3 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.25 mmol) in a 1:1 solution of 1,4-dioxane (12 mL):2M potassium carbonate (12 mL) was stirred for 18 h at 100° C. in a sealed tube. Upon cooling to room temperature, product precipitated out of solution which was filtered and dried to provide the title product as a light yellow powder (80%). ESMS [M+H]+: 334.2

Aufarbeitung

  1. customproduct precipitated out of solution which
  2. filtrationwas filtered
  3. customdried

Quellen und Nachweise

ORD-Eintrag
ord-8aa788e4231e4fc58b3620a43f930649
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07419988B2

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