4-amino-N-methylbenzene-1-sulfonamide → 4-(6-chloro-4-pyrrolidin-1-yl-pyridin-2-ylamino)-N-methyl-benzenesulfonamide

HRID 1437749Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1437749
Cl[C:2]1[CH:7]=[C:6]([N:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:5]=[C:4]([Cl:13])[N:3]=1.CC(C)([O-])C.[K+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.[NH2:66][C:67]1[CH:72]=[CH:71][C:70]([S:73]([NH:76][CH3:77])(=[O:75])=[O:74])=[CH:69][CH:68]=1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[Cl:13][C:4]1[N:3]=[C:2]([NH:66][C:67]2[CH:72]=[CH:71][C:70]([S:73]([NH:76][CH3:77])(=[O:75])=[O:74])=[CH:69][CH:68]=2)[CH:7]=[C:6]([N:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:5]=1

Komponenten

8

Edukt 4

HCID 743684-amino-N-methylbenzene-1-sulfonamideHCID 634876Binap, (A+-)-HCID 11644208HCID 11644208, VerbindungHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 116392174-(6-chloro-4-pyrrolidin-1-yl-pyridin-2-ylamino)-N-methyl-benzenesulfonamideAusbeute 24,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of 2,6-dichloro-4-pyrrolidino-pyridine (0.350 g, 1.62 mmol) in toluene (6 mL) were added potassium tert-butoxide (0.132 g, 1.18 mmol), palladium(II)-acetate (36.40 mg, 0.160 mmol), BINAP (32 mg, 0.514 mmol) and 4-amino-N-methyl-benzenesulfonamide (227 mg, 1.22 mmol) in a 10 mL reaction vessel. This reaction mixture was subjected the microwave irradiation, in which the microwave power was 250 W, to attain a reaction temperature of 150° C. After this reaction proceeded for 30 min, water (150 mL) was added to the reaction mixture and the reaction product was extracted with ethyl acetate. The organic layer was dried over sodium sulphate, filtered, and the filtrate concentrated under vacuum. The product was purified through column chromatography using 230-400 mesh silica gel (elution 20:80 acetone:petroleum ether) to afford the desired compound as a light brown solid (110 mg, yield 19%).

Aufarbeitung

  1. customin a 10 mL reaction vessel
  2. customthe microwave irradiation
  3. customa reaction temperature of 150° C
  4. extractionthe reaction product was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over sodium sulphate
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated under vacuum
  8. customThe product was purified through column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c614b00504ad44569f7b6db84973d737
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07622486B2

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