Potassium Carbonate → N-(3-Methoxybenzyl)-5-(1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)thiophene-3-carboxamide

HRID 2108755Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2108755
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][CH:18]=1)[CH2:6][NH:7][C:8]([C:10]1[CH:14]=[C:13](Br)[S:12][CH:11]=1)=[O:9].CC1(C)C(C)(C)OB([C:27]2[C:35]3[C:30](=[N:31][CH:32]=[CH:33][CH:34]=3)[N:29]([S:36]([C:39]3[CH:45]=[CH:44][C:42]([CH3:43])=[CH:41][CH:40]=3)(=[O:38])=[O:37])[CH:28]=2)O1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.CCOC(C)=O.O.[Pd].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>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][CH:18]=1)[CH2:6][NH:7][C:8]([C:10]1[CH:14]=[C:13]([C:27]2[C:35]3[C:30](=[N:31][CH:32]=[CH:33][CH:34]=3)[N:29]([S:36]([C:39]3[CH:45]=[CH:44][C:42]([CH3:43])=[CH:41][CH:40]=3)(=[O:38])=[O:37])[CH:28]=2)[S:12][CH:11]=1)=[O:9]

Komponenten

8

Edukt 3

HCID 11430Potassium CarbonateHCID 497589593-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridineHCID 57421982N-(3-Methoxybenzyl)-5-bromothiophene-3-carboxamide

Produkt 1

HCID 57633172N-(3-Methoxybenzyl)-5-(1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)thiophene-3-carboxamideAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 962WaterLösungsmittel2×HCID 80711,2-DimethoxyethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

N-(3-Methoxybenzyl)-5-bromothiophene-3-carboxamide (100 mg, 0.3 mmol), 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (122 mg, 0.3 mmol), potassium carbonate (125 mg, 0.9 mmol), and tetrakis(triphenylphosphine) palladium (0) (20 mg) were combined in 4 mL DME, 1 mL water, and heated to 160° C. in the microwave for 10 minutes. The reaction mixture was diluted with EtOAc and water. The organic layer was filtered through celite and concentrated to an oil which was purified by column chromatography on silica (20 to 60% EtOAc/hexanes) to give the product as a brown oil, 0.07 g, 0.14 mmol, 45% yield. MH+ 518.0

Aufarbeitung

  1. filtrationThe organic layer was filtered through celite
  2. concentrationconcentrated to an oil which
  3. customwas purified by column chromatography on silica (20 to 60% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-802ff1787b58405e8e331d338c9c74da
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07514448B2

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