Stannane → 4-(2,2-dimethylpropyl)-2-{1-[4-(5-fluoropyridin-2-yl)benzyl]vinyl}-N,N-dimethyl-1H-imidazole-1-sulfonamide

HRID 425430

Reaktionsgleichung

Reaktionsgleichung von HRID 425430
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][N:3]=1.Br[C:10]1[CH:34]=[CH:33][C:13]([CH2:14][C:15]([C:17]2[N:18]([S:27]([N:30]([CH3:32])[CH3:31])(=[O:29])=[O:28])[CH:19]=[C:20]([CH2:22][C:23]([CH3:26])([CH3:25])[CH3:24])[N:21]=2)=[CH2:16])=[CH:12][CH:11]=1.[SnH4]>COCCOC.C(OCC)(=O)C.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>[CH3:24][C:23]([CH3:26])([CH3:25])[CH2:22][C:20]1[N:21]=[C:17]([C:15]([CH2:14][C:13]2[CH:12]=[CH:11][C:10]([C:2]3[CH:7]=[CH:6][C:5]([F:8])=[CH:4][N:3]=3)=[CH:34][CH:33]=2)=[CH2:16])[N:18]([S:27]([N:30]([CH3:32])[CH3:31])(=[O:29])=[O:28])[CH:19]=1

Komponenten

7

Edukt 3

HCID 123161StannaneHCID 27831712-Bromo-5-fluoropyridineHCID 667056182-[1-(4-bromobenzyl)vinyl]-4-(2,2-dimethylpropyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide

Produkt 1

HCID 667058444-(2,2-dimethylpropyl)-2-{1-[4-(5-fluoropyridin-2-yl)benzyl]vinyl}-N,N-dimethyl-1H-imidazole-1-sulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysator2×HCID 80711,2-DimethoxyethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Pd(PPh3)4 (196 mg) was added to a solution of 2-bromo-5-fluoropyridine in DME (10 mL) at ambient temperature. After heating at 90° C. overnight the reaction mixture was cooled. 2-[1-(4-bromobenzyl)vinyl]-4-(2,2-dimethylpropyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide (110 mg) was added to the stannane solution followed by Pd(PPh3)4 (100 mg). After stirring at 95° C. overnight, the reaction mixture was cooled, diluted with ethyl acetate and washed with water. The organic phase was dried (sodium sulfate) and concentrated. Chromatography of the resulting crude product over silica eluting with 0-50% ethyl acetate/hexanes afforded 4-(2,2-dimethylpropyl)-2-{1-[4-(5-fluoropyridin-2-yl)benzyl]vinyl}-N,N-dimethyl-1H-imidazole-1-sulfonamide.

Aufarbeitung

  1. temperaturewas cooled
  2. temperaturethe reaction mixture was cooled
  3. washwashed with water
  4. dry with materialThe organic phase was dried (sodium sulfate)
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-6057f7179c1c4696909845307f399c60
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08106070B2

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