3-Methyl-2-(tributylstannyl)pyridine → tert-butyl methyl{[5-(3-methylpyridin-2-yl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}carbamate

HRID 1012527Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1012527
[CH3:1][C:2]1[C:3]([Sn](CCCC)(CCCC)CCCC)=[N:4][CH:5]=[CH:6][CH:7]=1.[C:21]([O:25][C:26](=[O:45])[N:27]([CH2:29][C:30]1[CH:34]=[C:33](Br)[N:32]([S:36]([C:39]2[CH:40]=[N:41][CH:42]=[CH:43][CH:44]=2)(=[O:38])=[O:37])[CH:31]=1)[CH3:28])([CH3:24])([CH3:23])[CH3:22]>C1(C)C=CC=CC=1.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>[CH3:28][N:27]([CH2:29][C:30]1[CH:34]=[C:33]([C:3]2[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][N:4]=2)[N:32]([S:36]([C:39]2[CH:40]=[N:41][CH:42]=[CH:43][CH:44]=2)(=[O:38])=[O:37])[CH:31]=1)[C:26](=[O:45])[O:25][C:21]([CH3:24])([CH3:22])[CH3:23]

Komponenten

5

Edukt 2

HCID 164270983-Methyl-2-(tributylstannyl)pyridineHCID 57522258tert-Butyl {[5-bromo-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate

Produkt 1

HCID 66974667tert-butyl methyl{[5-(3-methylpyridin-2-yl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}carbamateAusbeute 22,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of 3-methyl-2-(tributylstannyl)pyridine (1.0 g), tert-butyl{[5-bromo-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (563 mg) and tetrakis(triphenylphosphine)palladium (454 mg) in toluene was stirred under a nitrogen atmosphere at 120° C. for 30 hr. The mixture was cooled to room temperature and the solvent was evaporated under reduced pressure. The residue was purified by basic silica gel column chromatography (eluent:hexane-ethyl acetate=4:1) to give the title compound as a colorless oil (yield 129 mg, 22%).

Aufarbeitung

  1. customthe solvent was evaporated under reduced pressure
  2. customThe residue was purified by basic silica gel column chromatography (eluent:hexane-ethyl acetate=4:1)

Quellen und Nachweise

ORD-Eintrag
ord-7955d8f4e1bb4fe68584caa84e4b82d4
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07977488B2

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