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

HRID 1782353

Reaktionsgleichung

Reaktionsgleichung von HRID 1782353
[CH3:1][C:2]1[C:3]([Sn](CCCC)(CCCC)CCCC)=[N:4][CH:5]=[CH:6][CH:7]=1.Br[C:22]1[N:26]([S:27]([C:30]2[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=2)(=[O:29])=[O:28])[CH:25]=[C:24]([CH2:36][N:37]([CH3:45])[C:38](=[O:44])[O:39][C:40]([CH3:43])([CH3:42])[CH3:41])[CH:23]=1>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>[CH3:45][N:37]([CH2:36][C:24]1[CH:23]=[C:22]([C:3]2[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][N:4]=2)[N:26]([S:27]([C:30]2[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=2)(=[O:29])=[O:28])[CH:25]=1)[C:38](=[O:44])[O:39][C:40]([CH3:43])([CH3:41])[CH3:42]

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-7e097de107c94f40815c9390fe085e9f
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07498337B2

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