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Water → P-Anisidine

HRID 1043666
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1043666
IC1N2C(SC([NH:10][C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)=N2)=NC=1.CN(C1C=C(B(O)O)C=CC=1)C.C(=O)([O-])[O-].[Cs+].[Cs+].O>O1CCOCC1.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>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([NH2:10])=[CH:12][CH:13]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 962WaterHCID 10796Cesium carbonateHCID 27625273-(Dimethylamino)benzeneboronic acidHCID 67333843(5-Iodo-imidazo[2,1-b][1,3,4]thiadiazol-2-yl)-(4-methoxyphenyl)amine

Produkt 1

HCID 7732P-AnisidineAusbeute 32,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

(5-Iodo-imidazo[2,1-b][1,3,4]thiadiazol-2-yl)-(4-methoxyphenyl)amine (55 mg, 0.10 mmol) was suspended in 1,4-dioxane (1 mL) at room temperature and argon was bubbled into the mixture while tetrakis(triphenylphosphine)palladium(0) (0.011 mmol, 12 mg), 3-(N,N-dimethylamino)phenylboronic acid (0.202 mmol, 33 mg), cesium carbonate (0.268 mmol, 88 mg) and water (1 mL) were added. The mixture was deoxygenated for 10 minutes and heated under microwave irradiation at 140° C. for 1 hour. On cooling, the mixture was diluted with dichloromethane, adsorbed in silica and purified by column chromatography (Biotage™/Flash, silica, methanol:dichloromethane 0.2:9.8 to 2:8). The obtained residue was further purified by preparative HPLC to give {5-[3-dimethylaminophenyl)-imidazo[2,1-b][1,3,4]thiadiazol-2-yl]}-(4-methoxyphenyl)-amine as a white solid (4 mg, 7% yield).

Aufarbeitung

  1. additionwere added
  2. customThe mixture was deoxygenated for 10 minutes
  3. temperatureOn cooling
  4. additionthe mixture was diluted with dichloromethane
  5. custompurified by column chromatography (Biotage™/Flash, silica, methanol:dichloromethane 0.2:9.8 to 2:8)
  6. customThe obtained residue was further purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-24e5547bd4a74042876c3380997a7ef5
Quelldatensatz
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08563550B2

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